7-glycosyloxybenzopyran derivative and antiallergic agent containing the derivative as active ingredient

Abstract

A 7-glycosyloxybenzopyran derivative represented by the following formula (I) ##STR1## wherein, R is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group, R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group and R.sub.3 is a glycosyl group whose hydroxyl group is protected or not protected, selected from the group consisting of glucosyl, mannosyl and galactosyl groups, and physiologically acceptable salts thereof.

Description

FIELD OF THE INVENTION

This invention relates to 7-glycosybxybenzopyran derivatives which are obtained by glycosylation of the 7-position hydroxyl group of a benzopyran derivative with a hexose derivative. These compounds or physiologically acceptable salts thereof are useful as antiallergic agents.

BACKGROUND OF THE INVENTION

Benzopyran derivatives as the aglycon moiety of the 7-glycosyloxybenzopyran derivatives of the present invention have been disclosed for example in EP-A-0598117 by the present inventors, and similar benzopyran derivatives for example in J. Med. Chem., vol.31, pp.1473-1445, 1988, by Donald T. Witiak and in U.S. Pat. No. 4,845,121, but nothing about the 3- or 4-glycosyloxybenzopyran derivatives as their 7-position glycosides. In addition to this, nothing is known about the antiallergic activity of the 7-glycosyloxybenzopyran derivatives of the present invention and physiologically acceptable salts thereof.

Since antiallergic agents so far available commercially are not satisfactory in terms of efficiency, safety and bioavailability, studies on the development of antiallergic agents have been carried out: extensively. For example, a typical antiallergic agent, Tranilast (general name), requires high-dose administration for care of allergic disease, though its acute toxicity value (LD.sub.50) in mice is low (780 mg/kg), hence causing a problem of requiring caution at the time of its use because of the closeness between quantities of its efficacy and toxicity, namely its narrow safety range. Also, Disodium Cromoglicate (general name) as a well known antiasthamtic agent whose efficacy has been confirmed clinically is satisfactory in terms of its toxicity, but must be used by spray inhalation due to its extremely poor gastrointestinal absorbability. In addition, these known antiallergic agents are not effective on delayed type allergy, though they are effective on immediate type allergy. Chronic state of allergic diseases including asthma and atopic dermatitis is a serious problem, and the delayed type allergy is deeply concerned in the development of the chronic state. In consequence, a drug which is effective on both immediate type allergy and delayed type allergy is desirable as an antiallergic agent. As it is universally known, steroid is effective on both immediate type allergy and delayed type allergy but cause extremely serious side effects.

As has been described above, most of the antiallergic agents so far reported have various disadvantages, because they cannot show sufficient therapeutic effect because of the lack of efficacy on delayed type allergy, they are low in safety due to their narrow safety range, or their administration method is limited because of their poor gastrointestinal absorbability. In consequence, great concern has been directed toward the development of a drug which can be used in oral administration, has low toxicity and is effective on both immediate and delayed type allergies.

The inventors of the present invention have provided, by EP-A-0598117, a benzopyran derivative and an antiallergy agent which comprises the derivative as an active ingredient. This time, taking the aforementioned problems involved in the prior art into consideration, we contemplate providing a novel substance more useful as a drug and an antiallergic agent having low toxicity and excellent effect.

SUMMARY OF THE INVENTION

With the aim of providing a compound more useful as a drug, the inventors of the present invention have synthesized various glycosylated compounds of the benzopyran derivative disclosed in EP-A-0598117 by glycosylating its 7-position hydroxyl group with a hexose derivative and examined their antiallergic activity and safety. As the result, the present inventors have found that a 7-glycosyloxybenzopyran derivative represented by the following formula (I) is capable of showing markedly excellent antiallergic activity with low toxicity. The present invention has been accomplished on the basis of this finding. Accordingly, the present invention relates to a 7-glycosyloxybenzopyran derivative represented by the following formula (l) ##STR2## wherein R.sub.1 is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group, R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group and R.sub.3 is a glycosyl group whose hydroxyl group is protected or not protected, selected from the group consisting of glucosyl, mannosyl and galactosyl groups, to physiologically acceptable salts thereof and to an antiallergic agent which comprises the 7-glycosyloxybenzopyran derivative represented by the above formula (I) or a physiologically acceptable salt thereof as an active ingredient.

DETAILED DESCRIPTION OF THE INVENTION

Firstly, the 7-glycosyloxybenzopyran derivative represented by the formula (l) is described.

In the formula (I) of the present invention, R is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group.

Illustrative examples of the acyl group include alkanoyl groups such as acetyl, propionyl, butylyl, isobutylyl and the like groups, aroyl groups such as benzoyl group or a benzoyl group which may have a substituent group (p-methoxybenzoyl, p-methylbenzoyl, p-chlorobenzoyl or p-nitrobenzoyl for instance) and the like and acyl groups such as an alkoxycarbonyl group (methoxycarbonyl or ethoxycarbonyl for instance) and the like, of which an alkanoyl group is preferred and an acetyl group is particularly preferred.

Illustrative examples of the alkyl group include straight- or branched-chain noncyclic alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-methylpentyl, hexyl, octyl, decyl, dodecyl and the like alkyl groups preferably having 1 to 12, more preferably 1 to 10, carbon atoms.

Illustrative examples of the cycloalkyl group include straight- or branched-chain cycloalkyl groups such as unsubstituted cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl and cyclooctyl, and cycloalkyl groups substituted with alkyl groups such as 4-methylcyclohexyl and dimethylcyclohexyl, and the like, of which a cycloalkyl group having 5 to 8 of total number of carbon atoms of ring and side chain is preferred, and 4-methylcyclohexyl is particularly preferred.

Illustrative examples of the alkenyl group include straight- or branched-chain alkenyl groups such as vinyl, propenyl, pentenyl, hexenyl, heptenyl, octenyl, nonyl, decenyl, 3-methyl-2-butenyl, geranyl and the like alkenyl groups preferably having 2 to 1 0, more preferably 6 to 1 0, carbon atoms. Illustrative examples of the aralkyl group include those to be used as hydroxyl group protecting groups such as benzyl group or a benzyl group which may have a substituent group (p-methoxybenzyl, p-methylbenzyl, p-chlorobenzyl or p-nitrobenzyl for instance) and the like, of which unsubstituted benzyl group is particularly preferred.

In the formula (I) of the present invention, R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group.

Illustrative examples of the alkyl group include straight- or branched-chain alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-methylpentyl, hexyl, octyl, decyl, dodecyl and the like alkyl groups preferably having 1 to 12, more preferably 1 to 10, carbon atoms.

Illustrative examples of the cycloalkyl group include straight- or branched-chain cycloalkyl groups such as unsubstituted cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl and cyclooctyl, and cycloalkyl groups substituted with alkyl groups such as 4-methylcyclohexyl and dimethylcyclohexyl, and the like, of which a cycloalkyl group having 5 to 8 of total number of carbon atoms of ring and side chain is preferred, and 4-methylcyclohexyl is particularly preferred.

Illustrative examples of the alkenyl group include straight- or branched-chain alkenyl groups such as vinyl, propenyl, pentenyl, hexenyl, heptenyl, octenyl, nonyl, decenyl, 3-methyl-2-butenyl, geranyl and the like alkenyl groups preferably having 2 to 1 0, more preferably 6 to 1 0, carbon atoms.

Illustrative examples of the aralkyl group include those to be used as hydroxyl group protecting groups such as benzyl group or a benzyl group which may have a substituent group (pomethoxybenzyl, p-methylbenzyl, p-chlorobenzyl or p-nitrobenzyl for instance) and the like, of which unsubstituted benzyl group is particularly preferred.

The glycosyl group represented by R.sub.3 in the formula (I) is selected from glucosyl, mannosyl and galactosyl groups whose all or part of hydroxyl groups, which relates to binding of glycosyl group, may or may not be protected with a protecting group. In general, saccharides are known to have D and L stereoisomers which are also included in the present invention. The hexose derivatives to be used as the material of glycosyl groups are glucose, mannose and galactose whose all or part of hydroxyl groups may or may not be protected with a protecting group, of which an unprotected glycosyl group is preferred. The compound of the present invention, 7-glycosyloxybenzopyran derivative, is a compound in which any of these hexose derivatives is linked to the 7-position of a benzopyran derivative through glycoside bonding. Such a glycoside bonding may include .alpha.- and .beta.-binding types, and both of these binding types are included in the 7-glycosyloxybenzopyran derivative of the present invention.

With regard to the glycosyl group which is protected with a protecting group, preferred examples of the protecting group include those usually used as saccharide protecting groups such as acyl, aralkyl and the like groups. In this case, illustrative examples of the acyl group include alkanoyl groups such as acetyl, propionyl, butylyl, isobutylyl and the like groups, aroyl groups such as benzoyl group or a benzoyl group which may have a substituent group (p-methoxybenzoly, p-methylbenzoyl, p-chlorobenzoyl or p-nitrobenzoyl for instance) and the like and an alkoxycarbonyl group (methoxycarbonyl or ethoxycarbonyl for instance) and the like, of which an alkanoyl group is particularly preferred.

Illustrative examples of the aralkyl group include a benzyl group or a benzyl group which may have a substituent group (p-methoxybenzyl, p-methylbenzyl, p-chlorobenzyl or p-nitrobenzyl for instance) and the like.

Preferable protecting groups are a benzyl group and acetyl group, of which an acetyl group is particularly preferred. Though it varies depending on the type of the substituent groups of R.sub.1 and R.sub.2, galactose may be used as most preferred glycosyl group, followed by glucose and mannose in that order. Also, an unprotected glycosyl group is more preferable than its protected counterpart.

From the viewpoint of antiallergic activity, preferred examples of the 7-glycosyloxybenzopyran derivative of the present invention include a compound in which R.sub.1 is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group, R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group and R.sub.3 is glucosyl, mannosyl or galactosyl group, more preferred examples include a compound in which R.sub.1 is an alkyl group, a cycloalkyl group or an alkenyl group, R.sub.2 is a hydrogen atom and R.sub.3 is glucosyl, mannosyl or galactosyl group, most preferred examples include a compound in which R.sub.1 is an alkyl group, R.sub.2 is a hydrogen atom and R.sub.3 is glucosyl group, a compound in which R.sub.1 is a cycloalkyl group, R.sub.2 is a hydrogen atom and R.sub.3 is glucosyl group, a compound in which R.sub.1 is an alkenyl group, R.sub.2 is a hydrogen atom and R.sub.3 is glucosyl group, a compound in which R.sub.1 is an alkyl group, R.sub.2 is a hydrogen atom and R.sub.3 is galactosyl group, a compound in which R.sub.1 is a cycloalkyl group, R.sub.2 is a hydrogen atom and R.sub.3 is galactosyl group, and a compound in which R.sub.1 is an alkenyl group, R.sub.2 is hydrogen atom and R.sub.3 is galactosyl group.

The following summarizes a process for the production of the 7-glycosyloxybenzopyran derivative of the present invention.

The 7-glycosyloxybenzopyran derivative of the present invention represented by the formula (l) can be produced for example in the following manner in accordance with the following reaction scheme: ##STR3## wherein, R.sub.1, R.sub.2 and R.sub.3 are the same meanings as defined above, R.sub.4 represents an acyl group or an aralkyl group which is a protecting group of hydroxyl group of hexose derivative, and X represents a halogen atom.

As a first step, 7-hydroxybenzopyran derivative (1) disclosed by the present inventors in a prior application (EP-A-0598117) and a hexose halide derivative represented by the formula (2) are subjected to glycosylation. Each of the hexose halide derivatives can be prepared in accordance with a known method (cf. L. J. Haynes and F. H. Newth, Adv. Carbohydr. Chem., 10, 207 (1955); W. Korytnyk and J. A. Mills, J. Chem. Soc., 1959,636). A process for the production of the benzopyran derivative (1) to be used herein as a starting material is described in detail in EP-A-0598117. Namely, this derivative can be produced in accordance with the following reaction scheme: ##STR4##

Firstly, hydroxyl group of 2,4-dihydroxyacetophenone (a) is protected with benzyl group to obtain a compound (b). Next, carbon atoms of the thus obtained compound are increased by its reaction with dimethyl carbonate to convert it into a keto ester compound (c) which is subsequently allowed to react with benzoyl peroxide to obtain a compound (d). At this stage, the benzyl group used as a hydroxyl group protecting group is deblocked by hydrocracking and then treated with an acid to obtain a benzoyloxy compound (e). The thus obtained benzoyloxy compound (e) is then treated with a metal alkoxide in a non-aqueous system to effect elimination of benzoyl group, thereby obtaining a benzopyran derivative (f).

Benzopyran derivative (1) wherein R.sub.1 is other acyl group than benzoyl group is synthesized as follows. The hydroxyl groups at the 3-position and the 7-position of benzopyran derivative (f) are acylated and then the acyl group at the 7-position is selectively eliminated, whereby obtaining 7-hydroxy compound.

Benzopyran derivative (1) wherein the 4-position is substituted with an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group is synthesized as follows. The thus obtained benzopyran derivative (f) wherein the hydroxyl groups at the 3-position and the 7-position are protected is subjected to alkylation, cycloalkylation, alkenylation or aralkylation of the hydroxyl group at the 4-position.

Benzopyran derivative (1) wherein the 3-position is substituted with an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group is synthesized by selective elimination of the acyl group at the 3-position followed by alkylation, cycloalkylation, alkenylation or aralkylation. Benzopyran derivative (1) can be obtained by selectively introducing substituents.

Using the thus obtained benzopyran derivative (1) and the hexose derivative (2), glycosylation of the 7-position hydroxyl group is carried out in accordance with the known Koenigs-Knorr method. In this glycosylation, a metal catalyst may be used in the known Koenigs-Knorr method in order to accelerate the reaction, such as a silver salt, preferably silver oxide, silver carbonate or the like.

In this reaction, an organic solvent is used as a reaction solvent. Preferred examples of the solvent include ether solvents such as diethyl ether, tetrahydrofuran, dimethoxyethane, dioxane and the like, amide solvents such as dimethylformamide, dimethylacetamide and the like and nitrile solvents such as acetonitrile, propionitrile and the like. The reaction may be carried out at a temperature of from -20.degree. to 50.degree. C., preferably from 0.degree. to 30.degree. C., for a period of generally from 1 to 30 hours. In this way, the 7-glycosyloxybenzopyran derivative of the formula (3) is obtained.

When a compound having unprotected hydroxyl group on its glycosyl group is synthesized, deblocking reaction is carried out as a second step by debenzylation or deacylation of the hexose moiety in the formula (3), which can be attained in the usual way. That is, in the case of debenzylation, the reaction is effected by hydrocracking in an atmosphere of hydrogen gas making use of a metal catalyst.

Examples of the metal catalyst include palladium, platinum and the like catalysts which may be used in an amount of from 1 to 10% by weight based on the compound represented by the formula (3). The reaction in hydrogen gas may be carried out under a pressurized condition or under normal pressure. The reaction may be carried out generally in a solvent. Preferred examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, butanol and the like, ether solvents such as diethyl ether, tetrahydrofuran, dioxane and the like and acetic ester solvents such as methyl acetate, ethyl acetate, propyl acetate and the like. The reaction may be carried out at a temperature of from -10.degree. to 50.degree. C., preferably from 0.degree. to 30.degree. C., for a period of generally from 1 to 5 hours.

Also, deacylation can be effected by allowing the compound to react with a base as a deacylation agent which may be selected from hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide and the like and alkolate bases such as sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide and the like.

Preferred examples of the reaction solvent to be used in this reaction include lower alcohols such as methanol, ethanol, propanol and the like, ether solvents such as diethyl ether, tetrahydrofuran, dimethoxyethane, dioxane and the like and amide solvents such as dimethylformamide, dimethylacetamide and the like. The reaction temperature varies depending on the reaction reagent and solvent to be used and is within the range of preferably from -10.degree. to 50.degree. C., more preferably from 0.degree. to 30.degree. C. The reaction time is generally from 1 to 5 hours. The following compounds are illustrative examples of the thus obtained 7-glycosyloxybenzopyran derivatives of the present invention.

3,4-dihydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyrano2-one 3-propionyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzyloxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyrano2-one 3-(p-methoxybenzyloxy)-4-hydroxy 7-(p-.beta.-glucopyranosyloxy)-2 H-1-benzopyran-2-one 3,4-dihydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-acetyl-p-.beta.-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-hydroxy-7-(tetra-O-acetyl-p-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-hydroxy-7-(tetra-O-acetyl-p-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-hydroxy-7-(tetra-O-acetyl-.beta.-glucopyranosyloxy)-2H--benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-acetyl-I-.beta.-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)2H-1-benzopyrano2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dihydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-glucopyranosyloxy)-2 H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-glucopyranosyloxy)-2 H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dihydroxy-7-(.differential.-.beta.-mannopyranosyloxy)-2H-1-benzopyran-2-one -acetoxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(.alpha.-.beta.-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzyloxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2 H-1-benzopyran-2-one 3,4-dihydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(tetra-O-acetyl-G-.beta.-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-acetyl-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1 benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1 benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-bonzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-bonzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-benzolyl-.alpha.-D-mannopoyranosyloxy)-2H-1-benzopyran-2-one 3,4-dihydroxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(tetra-O-bonzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(tetra-O-bonzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-g(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(tetra-O-bonzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-benzyl-o-.beta.-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)o2H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-C)-benzyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dihydroxy-7-(-.beta.-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-oundecanyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzyloxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dihydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1 benzopyran-2-one 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H1-benzopyran-2-one 3-benzyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H 1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one -undecanyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dihydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-hydroxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-methoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-ethoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-isopropoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-butoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hexyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-octyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-decanyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-undecanyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-cyclohexyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(cis-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzyl-p-.beta.-galactopyranosyloxy)-2H-1-benzopyranosyloxy)-2H-1-benzopyran-2-one 3-(trans-4-methylcyclohexyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(3-hexenyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-geranyloxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3,4-dibenzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-(p-methoxybenzyloxy)-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-methoxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-ethoxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-isopropoxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-butoxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-hexyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-octyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-decanyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-undecanyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-cyclohexyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(cis-4-methylcyclohexyloxy)-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(trans-4-methylcyclohexyloxy)-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(3-hexenyloxy)-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-geranyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(p-methoxybenzyloxy)-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-methoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-ethoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-isopropoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-decanyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-undecanyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-cyclohexyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(cis-4-methylcyclohexyloxy)-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(trans-4-methylcyclohexyloxy)-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-geranyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(p-methoxybenzyloxy)-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-methoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-ethoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-isopropoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-decanyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-undecanyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-geranyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-(p-methoxybenzyloxy)-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-methoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-ethoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-isopropoxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-geranyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-methoxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-ethoxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-isopropoxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-butoxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hexyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyr anosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-octyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-decanyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-undecanyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(3-hexenyloxy)-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-geranyloxy-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(p-methoxybenzyloxy)-7-(tetra-O-benzoyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-methoxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-ethoxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-isopropoxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-butoxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-hexyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-octyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-decanyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-undecanyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-cyclohexyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(cis-4-methylcyclohexyloxy)-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(trans-4-methylcyclohexyloxy)-7-(.alpha.-D-mannopyranosyloxy)-2H 1-benzopyran-2-one 3-hydroxy-4-(3-hexenyloxy)-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-geranyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-methoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-ethoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-isopropoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-octyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-decanyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-undecanyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-cyclohexyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(cis-4-methylcyclohexyloxy)-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(trans-4-methylcyclohexyloxy)-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-geranyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(p-methoxybenzyloxy)-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-methoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-ethoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)o2H-1-benzopyran-2-one 3-benzoyloxy-4-isopropoxy-7-(tetrao-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-butoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hexyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-octyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-decanyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-undecanyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-geranyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-(p-methoxybenzyloxy)-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-methoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-ethoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-isopropoxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-hexyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-octyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-geranyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-methoxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-ethoxy-7-(tetra-O-bonzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-isopropoxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-butoxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hexyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-octyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-decanyloxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-undecanyloxy-7-(tetra-O-benzoyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(3-hexenyloxy)-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-geranyloxy-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(p-methoxybenzyloxy)-7-(tetra-O-benzolyl-.alpha.-D-mannopyranosyloxy)-H-1-benzopyran-2-one 3-hydroxy-4-methoxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-ethoxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-isopropoxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-butoxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-hexyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-octyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-decanyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-undecanyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-cyclohexyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(cis-4-methylcyclohexyloxy)-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(trans-4-methylcyclohexyloxy)-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(3-hexenyloxy)-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-geranyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-benzyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-hydroxy-4-(p-methoxybenzyloxy)-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-methoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-ethoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-isopropoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-decanyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-undecanyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-cyclohexyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(cis-4-methylcyclohexyloxy)-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(trans-4-methylcyclohexyloxy)-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-geranyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(p-methoxybenzyloxy)-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-methoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-ethoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-isopropoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-decanyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-undecanyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H--benzopyran-2-one 3-benzoyloxy-4-geranyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-benzoyloxy-4-(p-methoxybenzyloxy)-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-methoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H 1-benzopyran-2-one 3-propionyloxy-4-ethoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-isopropoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-proptonyloxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-(3-hexenyloxy)-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-propionyloxy-4-geranyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-methoxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-ethoxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-isopropoxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-butoxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-hexyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-octyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1 benzopyran-2-one 3-acetoxy-4-decanyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1 benzopyran-2-one 3-acetoxy-4-undecanyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(3-hexenyloxy)-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-geranyloxy-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one 3-acetoxy-4-(p-methoxybenzyloxy)-7-(tetra-O-benzoyl-.beta.-D-galactopyranosyloxy)-2-H-1-benzopyran-2-one

Physiolologically acceptable salts of these compounds are also included in the illustrative examples. The term "physiologically acceptable salts" as used herein means nontoxic alkali addition salts of, for example, the compounds cited above, which include sodium salts, potassium salts, magnesium salts, calcium salts, ammonium salts, nontoxic amine salts and the like. These physiologically acceptable salts can be produced by known methods and are also included in the present invention.

Since the 7-glycosyloxybenzopyran derivatives and physiologically acceptable salts thereof of the present invention (to be referred to as "the compound of the present invention" hereinafter) have a function to inhibit both immediate and delayed type allergic reactions as will be described later in Examples, they are useful as antiallergic agents for the treatment or prevention of various allergic diseases.

The term "allergic diseases" as used herein means allergic diseases resulting from excess activation of the biological immune mechanism caused by extrinsic or intrinsic antigens, which include immediate type asthma, delayed type asthma, bronchial asthma, pediatric asthma, atopic dermatitis, allergic dermatitis, urticaria, eczema, allergic conjunctivitis, allergic rhinitis, hay fever, food allergy, allergic gastroenteritis, allergic colitis, drug allergy, contact dermatitis, autoimmune disease and the like.

The antiallergic agent which comprises the compound of the present invention as an active ingredient can be administered orally or parenterally (for example, intravenous injection, subcutaneous injection, percutaneous absorption, rectal administration or the like). Such a pharmaceutical agent can be made into various dosage forms according to the purpose, such as tablets, capsules, granules, fine subtilaes, powders, troches, sublingual tablets, suppositories, ointments, injections, emulsions, suspensions, medicated syrups and the like. These dosage forms can be prepared in accordance with known techniques making use of pharmaceutically acceptable carriers which are commonly used in this type of drugs, such as excipients, bonding agents, disintegrators, lubricants, preservatives, anti-oxidative agents, isotonic agents, buffering agents, coating agents, sweetening agents, dissolving agents, bases, dispersing agents, stabilizing agents, coloring agents and the like.

Illustrative examples of these pharmaceutically acceptable carriers are listed in the following.

Firstly, as excipients, the following can be listed: starch and derivatives of starch (such as dextrin, carboxymethyl starch and the like), cellulose and derivatives of cellulose (such as methylcellulose, hydroxypropylmethylcellulose and the like), sugars (such as lactose, sucrose, glucose and the like), silicic acid and silicates (such as naturally occurring aluminum silicate, magnesium silicate and the like), carbonates (such as calcium carbonate, magnesium carbonate, sodium hydrogencarbonate and the like), aluminum magnesium hydroxide, synthetic hydrotalcite, polyoxyethylene derivatives, glycerin monostearate, sorbitan monooleic acid and the like.

As bonding agents, the following can be listed: starch and starch derivatives (such as alpha starches, dextrin and the like), cellulose and derivatives of cellulose (such as ethyl cellulose, sodium carboxymethyl cellulose, hydroxypropylmethyl cellulose and the like), gum arabic, traganth, gelatin, sugars (such as glucose, sucrose and the like), ethanol, polyvinyl alcohols and the like.

As disintegrators, the following can be listed: starch and starch derivatives (such as carboxymethyl starch, hydroxypropyl starch and the like), cellulose and cellulose derivatives (such as sodium carboxymethyl cellulose, crystal cellulose, hydroxypropylmethyl cellulose and the like), carbonates (such as calcium carbonate, calcium hydrogencarbonate and the like), traganth, gelatins, agar and the like.

As lubricants, the following can be listed: stearic acid, calcium stearate, magnesium stearate, talc, silicic acid and its salts (such as light silicic anhydrides, naturally occurring aluminum silicates and the like), titanium oxide, calcium hydrogen phosphate, dry aluminum hydroxide gel, macrogol and the like.

As preservatives, the following can be listed: p-hydroxybenzoates, sulfites (such as sodium sulfites, sodium pyrosulfites and the like), phosphates (such as sodium phosphates, calcium polyphosphates, sodium polyphosphates, sodium methaphosphate and the like), alcohols (such as chlorobutanol, benzyl alcohol and the like), benzalkonium chloride, benzethonium chloride, phenol, cresol, chlorocresol, dihydroacetic acid, sodium dihydroacetate, glycerin sorbic acid, sugars and the like.

As anti-oxidative agents, the following can be listed: sulfites (such as sodium sulfite, sodium hydrogen sulfite and the like), rongalite, erythorbic acid, L-ascorbic acid, cysteine, thioglycerol, butylhydroxyanisol, dibutylhydroxytoluene, propylgaltic acid, ascorbyl palmitate, dl-.alpha.-tocopherol and the like.

As isotonic agents, the following can be listed: sodium chloride, sodium nitrate, potassium nitrate, dextrin, glycerin, glucose and the like.

As buffering agents, the following can be listed: sodium carbonate, hydrochloric acid, boric acid, phosphates (such as sodium hydrogenphosphate) and the like.

As coating agents, the following can be listed: cellulose derivatives (such as hydroxypropyl cellulose, cellulose acetate phthalate, hydroxypropylmethyl cellulose phthalate and the like), shellac, polyvinylpyrrolidone, polyvinylpyridines (such as poly-2-vinylpyridine, poly-2-vinyl-5-ethylpyridine and the like), polyvinylacetyl diethylaminoacetate, polyvinyl alcohol phthalate, methacrylate, methacrylate copolymers and the like.

As sweetening agents, the following can be listed: sugars (such as glucose, sucrose, lactose and the like), sodium saccharin, sugar alcohols and the like.

As dissolving agents, the following can be listed: ethylenediamine, nicotinamide, sodium saccharin, citric acid, citrates, sodium benzoic acid, soaps, polyvinylpyrrolidone, polysolvates, sorbitan fatty acid esters, glycerin, propylene glycol, benzyl alcohols and the like.

As bases, the following can be listed: fats (such as lard and the like), vegetable oils (such as olive oil, sesame oil and the like), animal oil, lanolin acid, petrolatums, paraffin, wax, resins, bentonite, glycerin, glycol oils, higher alcohols (such as stearyl alcohol, cetanol) and the like.

As dispersing agents, the following can be listed: gum arabic, traganth, cellulose derivatives (such as methyl cellulose and the like), stearic acid polyesters, sorbitan sesquioleate, aluminum monostearate, sodium alginate, polysolvates, sorbitan fatty acid esters and the like.

Lastly, as stabilizing agents, the following can be listed: sulfites (such as sodium hydrogen sulfite and the like), nitrogen, carbon dioxide and the like.

Though the content of the compound of the present invention in these pharmaceutical preparations varies depending on the dosage forms, it may be contained preferably in a concentration of from 0.01 to 100% by weight.

Dose of the antiallergic agent of the present invention can be varied over a broad range depending on each mammal including human, mouse, rat, pig and the like, to be treated, extent of each disease, doctor's judgement and the like. In general, however, it may be administered in a dose of from 0.01 to 200 mg, preferably from 0.01 to 50 mg, more preferably from 0.05 to 10 mg, as the active ingredient per day per kg body weight in the case of oral administration or in a dose of from 0.01 to 10 mg, preferably from 0.01 to 5 mg, as the active ingredient per day per kg body weight in the case of parenteral administration. The daily dose described above may be used in one portion or in divided portions and changed optionally in accordance with the extent of diseases and doctor's judgement.

The following examples are intended to illustrate the preparation of the compounds of this invention and the pharmaceutical compositions of these compounds; however these examples are intended to illustrate the invention and not to be construed to limit the scope of the invention.

REFERENCE EXAMPLE 1

3-methoxy-4-benzyloxy-7-acetoxy-2H-1-benzopyran-2-one

To a mixture of 8.11 g of 3-methoxy-4-hydroxy-7-acetoxy-2H-l-benzopyran-2-one (27.8 mmol) and 5.71 g of benzyl bromide (33.4mmol) in 50 ml of DMF was added 4.61 g of sodium carbonate (33.4 mmol) under argon atmosphere, then the mixture was stirred at 50.degree. for 2 hours. The solid in the reaction mixture was filtered off, the filtrate was poured into 200 ml of water and extracted with 500 ml of benzene. The organic layler was concentrated in vacuo after drying over magnesium sulfate to give oily residue. The residue was purified on silica gel column chromatography (eluent: benzene/ethyl acetate=7/3) to give 3.50 g of the title compound. (yield=33%)

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 7.67 (d, 1H, J=8.8 Hz), 7.40 (m, 5H), 6.82 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.45 (s, 2H), 3.85 (s, 3H), 2.32 (s, 3H)

IR (KBr, cm.sup.-1): 1760, 1720, 1620, 1435, 1360, 1220

Elemental analysis for C.sub.19 H.sub.16 O.sub.6 Calculated (%): C 67.05;H 4.75;O 28.20 Found (%): C 67.15;H 4.63;O 28.22

REFERENCE EXAMPLE 2

3-methoxy-7-hydroxy-4-benzyloxy-2H-1-benzopyran-2-one

To a mixture of 3.64 g of 3-methoxy-4-benzyloxy-7-acetoxy-2H-1-benzopyran -2-one (10.7 mmol) in 50 ml of methanol was added 0.58 g of sodium methoxide (10.7 mmol) and the mixture was stirred at room temperature for 1 hour. Then 2.31 g of Amberlyst-15 (Trademark: Organo corp.) was added, and the mixture was stirred at room temperature for 1 hour. Amberlyst-15 was filterd off, the filtrate was concentrated under reduced pressure. The precipitate was obtained during concentration and filtered to give 2.59 g of the title compound. (yield=77%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.30 (bs, 1H), 7.67 (d, 1H, J=8.8 Hz), 7.40 (m, 5H), 6.72 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.45 (s, 2H), 3.78 (s, 3H)

IR (KBr, cm.sup.-1): 3200, 1760, 1720, 1620, 1435, 1360, 1220

Elemental analysis for C.sub.17 H.sub.14 O.sub.5 Calculated (%): C 68.45;H 4.73;O 26.82 Found (%): C 68.25;H 4.73;O 27.02

REFERENCE EXAMPLE 3

3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one

To a mixture of 17.31 g of 4-butoxy-3, 7-diacetoxy-2H-l-benzopyran-2-one (51.79 mmol) in 170 ml of methanol was added 2.66 g of sodium methoxide (49.20 mmol) and the reaction mixture was stirred at room temperature for 3 hours. Then 22.36 g of Amberlyst-15 was added, and the mixture was stirred at room temperature for 1 hour. Amberlyst-15 was filtered off and the filtrate was concentrated under reduced pressure to give a crystalline product. The product was reprecipitated from tertahydrofuran and hexane to give 12.87 g of the title compound. (yield=85%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.60 (s, 1H), 7.64 (d, 1H, J=8.8 Hz), 6.87 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 6.75 (d, 1H, J=2.4 Hz), 4.42 (t, 2H, J=6.2 Hz), 2.33 (s, 1.80.about.1.70 (m, 2H), 1.55.about.1.40 (m, 2H), 0.94 (t, 3H, J=7.4 Hz)

IR (KBr, cm.sup.-1): 3200, 2950, 1760,1690, 1620, 1410, 1340

Elemental analysis for C.sub.15 H.sub.16 O.sub.6 Calculated (%): C 61.64;H 5.52;O 32.84 Found (%) :C 61.60;H 5.53;O 32.87

REFERENCE EXAMPLE 4

3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one

In accordance with Reference Example 3, 30.00 g of 4-hexyloxy-3, 7-diacetoxy-2H-l-benzopyran-2-one (82.79 mmol) was used instead of 4-butoxy-3,7-diacetoxy-2H-l-benzopyran-2-one, 22.01 g of the title compound was obtained. (yield=83%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.63 (s, 1H), 7.63 (d, 1H, J=8.8 Hz), 6.86 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 6.74 (d, 1H, J=2.4 Hz), 4.41 (t, 2H, J=6.2 Hz), 2.32 (s,3H) 180.about.1.70 (m, 2H), 1.50.about.1.25 (m, 4H), 0.87 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3200, 2930, 1760, 1690, 1620, 1410, 1340

Elemental analysis for C.sub.17 H.sub.20 O.sub.6 Calculated (%): C 63.74;H 6.29;O 29.97 Found (%): C 63.76;H 6.26;O 29.98

REFERENCE EXAMPLE 5

3-acetoxy-4-octyloxy-7-hydroxy-2H-1-benzopyran-2-one

In accordance with Reference Example 3, 30.00 g of 4-octyloxy-3, 7-diacetoxy-2H-l-benzopyran-2-one (76.84 mmol) was used instead of 4-butoxy-3,7-diacetoxy-2H-l-benzopyran-2-one, 23.19 g of the title compound was obtained. (yield=87%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.62 (s, 1H), 7.63 (d, 1H, J=8.8 Hz), 6.86 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 6.74 (d, 1H, J=2.4 Hz), 4.46 (t, 2H, J=6.4 Hz), 2.32 (s,3H), 1.80.about.1.65 (m, 2H), 1.50.about.1.10 (m, 6H), 0.85 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3200, 2900, 1760, 1690, 1620, 141 0, 1340

Elemental analysis for C.sub.19 H.sub.24 O.sub.6 Calculated (%): C 65.50;H 6.94;O 27.55 Found (%) :C 65.38;H 6.98;0 27.64

EXAMPLE 1

3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 1)

1.53 g of 3-methoxy-4-benzyloxy-7-hydroxy-2H-1-benzopyran-2-one (5.12 mmol) and 4.21 g of 2, 3, 4, 6-tetra-O-acetyl-.alpha.-D-glucopyranosyl bromide (10.23 mmol) were dissolved in 20 ml of acetonitrile at room temperature under argon atmosphere. To this solution, 1.19 g of silver (l) oxide (5.12 mmol) and 13.77 g of molecular sieve 4A (Merck) were added and the mixture was stirred at room temperature for 2 hours. After filtration, the filtrate was concentrated under reduced pressure, giving an oily residue. Purification of the residue on silica gel column chromatography (eluent: benzene/ethyl acetate=2/1) gave 1.77 g of the title compound (1). (yield=55%)

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.20.about.7.40 (m, 5H), 6.88 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.42. (s, 2H), 5.25.about.5.35 (m, 2H), 5.14 (t, 1H, J=(d, 1H, J=8.0 Hz), 4.21.about.4.28 (m, 2H), 3.82.about.3.85 (m, 1H), 3.78 (s, 3H), 2.02.about.2.22 (m, 12H)

IR (KBr, cm.sup.-1): 1750, 1620, 1435, 1360, 1240

Elemental analysis for C.sub.31 H.sub.32 O.sub.14 Calculated (%) :C 59.23;H 5.09;O 35.68 Found (%): C 59.40;H 4.95;O 35.65

EXAMPLE 2

3-methoxy-4-hydroxy-7-(tetra-O-acety-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 2)

Under hydrogen atmosphere, a mixture of 2.19 g of 3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (3.48 mmol) and 0.22 g of 10% palladium on activated carbon in 20 ml of ethyl acetate was stirred at room temperature for 2 hours. The catalyst was filtered off, and the filtrate was evaporated to give a crude product. After washing the crude product with diethyl ether, 1.59 g of the title compound (2) was obtained. (yield-85%)

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 10.50 (bs, 1H), 7.70 (d, 1H, J=8.8 Hz), 6.88 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.25.about.5.35 (m, 2H), 5.14 (t, 1H, J=8.0 Hz), 4.93 (d, 1H, J=8.0 Hz), 4.21.about.4.28 (m, 2H), 3.82.about.3.85 (m, 1H), 3.78 (s, 3H), 2.02.about.2.22 (m, 12H)

IR (KBr, cm.sup.-1): 3250, 1750, 1620, 1435, 1360, 1240

Elemental analysis for C.sub.24 H.sub.26 O.sub.14 Calculated (%): C 53.53;H 4.83;O 41.64 Found (%): C 53.40;H 4.90;O 41.70

EXAMPLE 3

3-methoxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 3)

Under argon atmosphere, to a mixture of 0.58 g 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (1.07 mmol) in 12 ml of methanol was added 0.15 g of sodium methoxide at 5.degree. and followed by stirring at room temperature for 1 hour. Then 0.75 g of Ambrtlyst-15 was added and the mixture was stirred at room temperature for 1 hour. After dissolving a precipitate generated during neutralization by adding excess methanol, Amberlyst-15 was filtered off and the filtrate was concentrated in vacuo to give a precipitate. Filtration gave 0.31 g of the title compound (3). (yield=77%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J=8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J=8.4 Hz), 4.98 (bs, 4H), 4.83 (d, 1H, J=7.6 Hz), 3.85 (s, 3H 1H, J=7.6 Hz), 3.51 (d, 1H, J=7.6 Hz), 3.41 (m, 1H), 3.31.about.3.20 (m, 3H)

lgR (KBr, cm.sup.-1): 3350, 1660, 1630, 1580, 1270

Elemental analysis for C.sub.16 H.sub.10 O.sub.10 Calculated (%): C 51.89;H 4.90;O 43.21 Found (%): C 51.52;H 4.85;O 43.63

EXAMPLE 4

3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one(compound 4)

In accordance with Example 1,4.21 g of 2,3,4,6-tetra-O-acetyl-.beta.-D-mannopyranosyl bromide (10.23 mmol) was used instead of 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl bromide, 1.88 g of the title compound (4) was obtained. (yield=58%)

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 7.67 (d, 1H, J=8.4 Hz), 7.20.about.7.40 (m, 5H), 6.95 (s, 1H), 6.94 (d, 1H, J=8.4 Hz), 6.00 (s, 1H), 5.55 (m, 2H), 5.45 (s, 2H), 5.40 (m,5H), 6.95 (s, 1H), (m, 2H), 4.15 (s, 1H), 3.75(s, 3H), 2.02.about.2.22 (m, 12H)

IR (KBr, cm.sup.-1): 1750, 1620, 1435, 1360, 1240

Elemental analysis for C.sub.31 H.sub.32 O.sub.14 Calculated (%): C 59.23;H 5.09;O 35.68 Found (%): C 59.40;H 5.15;O 35.45

EXAMPLE 5

3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 5)

In accordance with Example 1,4.21 g of 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide (10.23 mmol) was used instead of 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl bromide, 1.82 g of title compound (5) was obtained. (yield=56%)

.sup.1 -NMR (CDCl.sub.3, .delta.-TMS): 7.72 (d, 1H, J=8.8 Hz), 7.20.about.7.40 (m, 5H), 6.88 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 6.01 (s, 1H), 5.55 (m, 2H), 5.45 (s, 2H), 5.40 (s,1H), 5.16.about.5.25 (m, 1H), 4.10.about.4.20 (m, 2H), 3.90 (s, 3H), 2.02.about.2.22 (m, 12H)

IR (KBr, cm.sup.-1): 1750, 1620, 1435, 1360, 1240

Elemental analysis for C.sub.31 H.sub.32 O.sub.14 Calculated (%) :C 59.23;H 5.09;O 35.68 Found (%) :C 59.42;H 5.15;O 35.43

EXAMPLE 6

3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one (compound 6)

In accordance with Example 2,3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one was used instead of 3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one, 0.321 g the title compound (6) was obtained. (yield=81%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J=8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J=8.4 Hz), 6.00 (s, 1H), 5.55 (m, 2H), 5.40 (m, 1H), 4.23 (m, 2H), 4.15 (s, 1H), 3.75 (s, 3H), 2.02.about.2.22 (m, 12H)

IR (KBr, cm.sup.-1): 3350, 1660, 1630, 1580, 1270

Elemental analysis for C.sub.24 H.sub.26 O.sub.14 Calculated (%): C 53.53;H 4.83;O 41.64 Found (%): C 53.42;H 4.55;O 42.03

EXAMPLE 7

3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 7)

In accordance with Example 2,3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one was used instead of 3-methoxy-4-benzyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one, 0.309 g of the title compound (7) was obtained. (yield=78%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J=8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J=8.4 Hz), 4.85 (d, 1H, J=7.6 Hz), 3.85 (s, 3H), 3.65 (d, 1H, J=7.6 Hz), 3.51 (d, 1H, J=7.6 Hz), 3.41 (m, 1H), 3.20.about.3.40 (m, 3H), 2.05.about.2.22 (m, 12H)

IR (KBr, cm.sup.-1): 3350, 1660, 1630, 1580, 1270

Elemental analysis for C.sub.24 H.sub.26 O.sub.14 Calculated (%): C 53.53;H 4.83;O 41.64 Found (%): C 53.42;H 4.55;O 42.03

EXAMPLE 8

3-methoxy-4-hydroxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one (compound 8)

In accordance with Example 3, 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one was used instead of 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one, 0.310 g of the title compound (8) was obtained. (yield=78%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 11.40 (bs, 1H), 7.67 (d, 1H, J=8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J=8.4 Hz), 6.00 (s, 1H), 5.55 (m, 2H), 5.40 (m, 1H), 4.98 (bs, 4H), 4.23 (m, 2H), 4.15 (s, 1H), 3.75 (s, 3H)

IR (KBr, cm.sup.-1): 3350, 1660, 1630, 1580, 1270

Elemental analysis for C.sub.16 H.sub.18 O.sub.10 Calculated (%): C 51.89;H 4.90;O 43.21 Found (%): C 51.52;H 4.85;O 43.63

EXAMPLE 9

3-methoxy-4-hydroxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 9)

In accordance with Example 3, 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one was used instead of 3-methoxy-4-hydroxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one, 0.295 g of the title compound (9) was obtained. (yield=74%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 11.25 (bs, 1H), 7.67 (d, 1H, J=8.4 Hz), 6.95 (s, 1H), 6.94 (d, 1H, J=8.4 Hz), 5.00 (bs, 4H), 4.85 (d, 1H, J=7.6 Hz), 3.85 (s, 3H), 3.65 (d, 1H, J=7.6 Hz), 3.51 (d, 1H, J=7.6 Hz), 3.41 (m, 1H), 3.20.about.3.40 (m, 3H)

IR (KBr, cm.sup.-1): 3350, 1660, 1630, 1580, 1270

Elemental analysis for C.sub.16 H.sub.18 O.sub.10 Calculated (%): C 51.89;H 4.90;O 43.21 Found (%) :C 51.65;H 4.85;O 43.50

EXAMPLE 10

3-acetoxy-4-benzyloxy-7-(tetra-O-benzyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 10)

In accordance with Example 1, 1.00 g of 3-acetoxy-4-benzyloxy-7-hydroxy-2H-1-benzopyran-2-one (3.06 mmol) and 2.70 g of 2, 3, 4, 6-tetra-O-benzyl-.alpha.-D-glucopyranosyl bromide (4.43 mmol) were used instead of 3-methoxy-4-benzyloxy-7-hydroxy-2H-1-benzopyran-2-one and 2, 3, 4, 6-tetra-O-acetyl-.alpha.-D-glucopyranosyl bromide, 1.52 g of the title compound (10) was obtained. (yield=58%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.67 (d, 1H, J=8.8 Hz), 7.15.about.7.60 (m, 25H), 6.88 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.42 (s, 2H), 5.25.about.5.35 (m, 2H), 5.20 (m, 8H), 5.14 (t, 1H, J=8.0 Hz), 4.93 (d, 1H, J=8.0 Hz), 4.21.about.4.28 (m, 2H), 3.82.about.3.85 (m, 1H), 2.38 (s, 3H)

IR (KBr, cm.sup.-1): 1760, 1640, 1600, 1450, 1380

Elemental analysis for C.sub.52 H.sub.48 O.sub.11 Calculated (%): C 73.58;H 5.66;O 20.76 Found (%): C 73.53;H 5.78;O 20.69

EXAMPLE 11

3-acetoxy-4-hydroxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 11)

Under argon atmosphere, 1.50 g of 3-acetoxy-4-benzyloxy-7-(tetra-O-benzyloxy-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (1.77 mmol) was dissolved in 150 ml of tetrahydrofuran at room temperature, and 0.15 g of 10% palladium on activated carbon was added. After argon gas was replaced with hydrogen gas, the reaction mixture was stirred at room temperature for 2 hours. The catalyst was filtered off, and the filtrate was evaporated to give a crystalline product. 0.662 g of the title compound (11) was obtained after reprecipitation from tetrahydrofuran and hexane. (yield=94%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.5 (bs, 1H), 7.70 (d, 1H, J=8.4 Hz), 6.70.about.6.90 (m, 2H), 5.80 (bs, 1H), 5.32 (d, 1H, J=7.2 Hz), 5.19 (s, 1H), 5.02 (s, 1H), 4.50 (s, 1H), 3.10.about.3.70 (m, 6H), 2.33 (s, 3H)

IR (KBr, cm.sup.-1): 3400, 1780, 1670, 1610, 1580, 1270

Elemental analysis for C.sub.17 H.sub.18 O.sub.11 Calculated (%): C 51.26;H 4.52;O 44.22 Found (%): C 51.27;H 4.51;O 44.22

EXAMPLE 12

3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 12)

11.74 g of 3-acetoxy-4-butoxy-7-hydroxy-2H-l-benzopyran-2-one (40.18 mmol) and 24.74 g 2, 3, 4, 6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide (60.27 mmol) were dissolved in 360 ml of acetonitrile at room temperature under argon atmosphere. To this solution, 11.17 g of silver (I) oxide (48.21 mmol) and 106 g of molecular sieve 4A were added and the mixture was stirred at room temperature for 4 hours. After filtration, the filtrate was concentrated under reduced pressure, giving an oily residue. Purification of the residue on silica gel column chromatography (eluent:hexane/ethyl acetate=2/1) gave 3.00 g of the title compound (12). (yield=52%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=2.4 Hz), 5.20.about.5.30 (m, 2H), 4.52 (t, 1H, J=6.6 Hz), 4.46 (t, 2H, J=6.0 Hz), 4.11 (d, 2H, J=6.0 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H), 1.70.about.1.80 (m, 2H), 1.40.about.1.55 (m, 2H), 0.93 (t, 3H, J=3.6 Hz)

IR (KBr, cm.sup.-1): 2950, 1750, 1630, 1370, 1240

Elemental analysis for C.sub.29 H.sub.34 O.sub.15 Calculated (%): C 55.95;H 5.50;O 38.55 Found (%): C 55.84;H 5.58;O 38.58

EXAMPLE 13

3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 13)

In accordance with Example 12, 12.86 g of 3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one (40.18 mmol) and 24.78 g of 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl bromide (60.27 mmol) were used instead of 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide, 13.58 g of the title compound (13) was obtained. (yield=52%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.45 (t, 2H, J=6.0 Hz), 4.10.about.4.40 (m, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.70.about.1.80 (m, 2H), 1.25.about.1.50 (m, 6H), 0.88 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 2950, 1750, 1620, 1370, 1240

Elemental analysis for C31H38015 Calculated (%): C 58.13;H 4.41;O 37.47 Found (%): C 58.20;H 4.45;O 37.35

EXAMPLE 14

3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one (compound 14)

In accordance with Example 12, 6.00 g of 3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one (18.73 mmol) and 11.55 g of 2,3,4,6-tetra-O-acetyl-.alpha.-D-mannopyranosyloxy bromide (28.10 mmol) were used instead of 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide, 3.66 g of the title compound (14) was obtained. (yield=30%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.78 (d, 1H, J=8.8 Hz), 7.15.about.7.30 (m, 2H), 5.94 (s, 1H), 5.35.about.5.45 (m, 2H), 5.13 (t, 1H, J=10.0 Hz), 4.45 (t, 2H, J=5.9 Hz), 3.90.about.4.20 (m, 3H), 2.34 (s, 3H), 2.18 (s, 3H), 2.05 (s, 3H), 2.00 (s, 3H), 1.92 (s, 3H), 1.70.about.1.80 (m, 2H), 1.25.about.1.50 (m, 6H), 0.88 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2950, 1750, 1630, 1370, 1240

Elemental analysis for C.sub.31 H.sub.38 O.sub.15 Calculated (%): C 58.13;H 4.41;O 37.47 Found (%): C 58.19;H 4.39;O 37.42

EXAMPLE 15

3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 15)

In accordance with Example 12, 4.50 g of 3-acetoxy-4-hexyloxy-7-hydroxy-2H-1-benzopyran-2-one (14.05 mmol) and 8.66 g of 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyronosyloxy bromide (21.07 mmol) were used instead of 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide, 4.66 g of the title compound (15) was obtained. (yield=51%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=9.2 Hz), 7.05.about.7.15 (m, 2H), 5.66 (d, 1H, J=7.2 Hz), 5.20.about.5.40 (m, 2H), 4.50.about.4.55 (m, 3H), 4.45 (t, 2H, J=6.2 Hz), 4.12 (t, 2H, J=6.4 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.03 (s, 3H), 1.97 (s, 3H), 1.70.about.1.80 (m, 2H), 1.25.about.1.50 (m, 6H), 0.88 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 2930, 1750, 1620, 1370, 1230

Elemental analysis for C31H38015

Calculated (%): C.sub.31 H.sub.38 O.sub.15 Found (%): C 58.16;H 4.45;O 37.39

EXAMPLE 16

3-acetoxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 16)

In accordance with Example 12, 14.00 g of 3-acetoxy-4-octyloxy-7-hydroxy-2H-1-benzopyran-2-one (40.28 mmol) and 24.84 g of 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyloxy bromide (60.41 mmol) were used instead of 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide, 13.65 g of the title compound (16) was obtained. (yield=50%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.76 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.10.about.5.15 (m, 1H), 5.04 (t, 1H, J=9.8 Hz), 4.45 (t, 2H, J=6.0 Hz), 4.05.about.4.35 (m, 3H), 2.34 (s, 3H), 2.00.about.2.05 (m, 9H), 1.99 (s, 3H), 1.70.about.1.80 (m, 2H), 1.20.about.1.50 (m, 10H), 0.85 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 2920, 1740, 1630, 1610, 1370, 1230

Elemental analysis for C.sub.33 H.sub.42 O.sub.15 Calculated (%): C 58.40;H 6.24;O 35.36 Found (%): C 58.16;H 6.19;O 35.65

EXAMPLE 17

3-acetoxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 17)

In accordance with Example 12, 14.00 g of 3-acetoxy-4-octyloxy-7-hydroxy-2H-1-benzopyran-2-one (40.28 mmol) and 24.84 g of 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide (60.41 mmol) were used instead of 3-acetoxy-4-butoxy-7-hydroxy-2H-1-benzopyran-2-one and 2,3,4,6-tetra-O-acetyl-.alpha.-D-galactopyranosyloxy bromide, 14.47 g of the title compound (17) was obtained. (yield=53%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.76 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 7.04 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=7.2H 5.20.about.5.40 (m, 2H), 4.42 (t, 1H, J=6.4 Hz), 4.45 (t, 2H, J=6.4 Hz), 4.11 (d, 2H, J=6.0 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.03 (s, 3H), 1.97 (s, 3H), 1.70.about.1.80 (m, 2H), 1.20.about.1.50 (m, 1 OH), 0.85 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 2930, 1750, 1620, 1370, 1230

Elemental analysis for C.sub.33 H.sub.42 O.sub.15 Calculated (%): C 58.40;H 6.24;O 35.36 Found (%): C 58.51;H 6.29;O 35.20

EXAMPLE 18

3-hydroxy-4-butoxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 18)

Under argon atmosphere, to a mixture of 19.07 g 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (30.63 mmol) in 380 ml of methanol was added 3.31 g of sodium methoxide (61.26 mmol) at 5.degree. and followed by stirring at room temperature for 1 hour. Then 27.85 g of Ambrtlyst-15 was added and the mixture was stirred at room temperature for 1 hour. Amberlyst-15 was filtered off and the filtrate was evaporated to give a crystalline product. 10.18 g of the title compound (18) was obtained after reprecipitation from ethanol. (yield=81%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.18 (s, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.00.about.7.10 (m, 2H), 5.20 (d, 1H, J=5.6 Hz), 4.91 (d, 1H, J=8.0 Hz), 4.88 (d, 1H, J=5.2 Hz), 4.67 (t, 1H, J=5.2 Hz), 4.52 (d, 1H, J=4.4 Hz), 4.48 (t, 2H, J=6.4 Hz), 3.40.about.3.75 (m, 6H), 1.65.about.1.75 (m, 2H), 1.40.about.1.50 (m, 2H), 0.93 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3400, 2950, 2930, 2860, 1680, 1640, 1610, 1250

Elemental analysis for C.sub.19 H.sub.24 O.sub.10 Calculated (%): C 55.34;H 5.87;O 38.80 Found (%): C 55.41;H 5.81;O 38.78

EXAMPLE 19

3-hydroxy-4-hexyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 19)

In accordance with Example 18, 10.94 g of 3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (16.81 mmol) was used instead of 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one, 6.66 g of the title compound (19) was obtained. (yield=90%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.00.about.7.10 (m, 2H), 5.37(bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.47 (t, 2H, J=6.2 Hz), 3.10.about.3.75 (m, 6H), 1.65.about.1.80 (m, 2H), 1.20.about.1.50 (m, 6H), 0.87 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1700, 1640, 1610, 1260

Elemental analysis for C.sub.21 H.sub.28 O.sub.10 Calculated (%): C 57.27;H 6.41;O 36.33 Found (%): C 55.25;H 6.49;0 38.46

EXAMPLE 20

3-hydroxy-4-hexyloxy-7-(.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one (compound 20)

In accordance with Example 18, 13.40 g of 3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.alpha.-D-mannopyranosyloxy)-2H-1-benzopyran-2-one (20.60 mmol) was used instead of 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one, 7.62 g of the title compound (20) was obtained. (yield=84%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.8 (bs, 1H), 4.77 (bs, 1H), 4.47 (t, 2H, J=6.4 Hz), 3.85 (s, 1H), 3.20.about.3.75 (m, 6H), 1.65.about.1.80 (m, 2H), 1.20.about.1.50 (m, 6H), 0.87 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C21H28O.sub.10 Calculated (%): C 57.27;H 6.41;O 36.33 Found (%): C 57.38;H 6.40;O 36.22

EXAMPLE 21

3-hydroxy-4-hexyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 21)

In accordance with Example 18, 12.57 g of 3-acetoxy-4-hexyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (19.32 mmol) was used instead of 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one, 7.55 g of the title compound (21) was obtained. (yield=89%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.00.about.7.10 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs 1H), 4.47 (t, 2H, J=6.6 Hz), 3.25.about.3.65 (m, 6H), 1.70.about.1.80 (m, 2H), 1.20.about.1.50 (m, 6H), 0.87 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3400, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.21 H.sub.28 O.sub.10 Calculated (%): C 57.27;H 6.41;O 36.33 Found (%): C 57.16;H 6.46;O 36.38

EXAMPLE 22

3-hydroxy-4-octyloxy-7-(.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (compound 22)

In accordance with Example 18, 10.95 g of 3-acetoxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-glucopyranosyloxy)-2H-1-benzopyran-2-one (16.13 mmol) was used instead of 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one, 6.95 g of the title compound (22) was obtained. (yield=92%)

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.19 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.00.about.7.10 (m, 2H), 5.37 (bs, 1H)5.11 (bs, 1H), 5.05 (bs, 1H), 4.95 (d, 1H, J=7.2 Hz), 4.59 (bs, 1H), 4.46 (t, 2H, J=6.4 Hz), 3.10.about.3.75 (m, 6H), 1.65.about.1.80 (m, 2H), 1.15.about.1.50 (m, 10H), 0.85 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3350, 2920, 2850, 1700, 1640, 1610, 1250

Elemental analysis for C.sub.23 H.sub.32 O.sub.10 Calculated (%): C 58.97;H 6.88;O 34.15 Found (%): C 58.92;H 6.87;O 34.21

EXAMPLE 23

3-hydroxy-4-octyloxy-7-(.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (compound 23)

In accordance with Example 18, 20.67 g of 3-acetoxy-4-octyloxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one (30.46 mmol) was used instead of 3-acetoxy-4-butoxy-7-(tetra-O-acetyl-.beta.-D-galactopyranosyloxy)-2H-1-benzopyran-2-one, 12.47 g of the title compound (23) was obtained. (yield=87%)

.sup.1 H-NMR (DMSO-d.sub.6, -TMS): 9.15 (bs, 1H), 7.60 (d, 1H, J=8.4 Hz), 7.00.about.7.10 (m, 2H), 5.21 (bs, 1H), 4.91 (d, 1H, J=8.0 Hz), 4.88 (bs, 1H), 4.66 (bs, 1H), 4.52 (d, 1H, J=3.6 Hz), 4.47 (t, 2H, J=6.6 Hz), 3.10.about.3.75 (m, 6H), 1.65.about.1.80 (m, 2H), 1.15.about.1.50 (m, 10H), 0.85 (t, 3H, J=6.6 Hz)

IR (KBr, cm.sup.-1): 3400, 2910, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.23 H.sub.32 O.sub.10 Calculated (%): C 58.97;H 6.88;O 34.15 Found (%): C 58.99;H 6.92;O 34.09

EXAMPLE 24.about.160

The following Tables show 7-glycopyranosyloxy benzopyran derivatives (24).about.(160) obtained by the methods described in Examples. The abbreviations used in this table are as follows: Glc, glucopyranosyl group; Man, mannopyranosyl group; Gal, galactopyranosyl group; R.sub.4, protecting group of sugar.

TABLE 1__________________________________________________________________________ referential yieldexample compound example R.sub.1 R.sub.2 R.sub.3 R.sub.4 (%)__________________________________________________________________________24 24 1 CH.sub.3 benzyl Glc(.beta.-D form) benzyl 5225 25 1 C.sub.4 H.sub.9 benzyl Glc(.beta.-D form) benzyl 6026 26 1 C.sub.6 H.sub.13 benzyl Glc(.beta.-D form) acetyl 5127 27 1 C.sub.8 H.sub.17 benzyl Glc(.beta.-D form) acetyl 5328 28 1 C.sub.10 H.sub.21 benzyl Glc(.beta.-D form) acetyl 5129 29 1 C.sub.12 H.sub.25 benzyl Glc(.beta.-D form) acetyl 5830 30 1 (CH.sub.3).sub.2 CH benzyl Glc(.beta.-D form) acetyl 5931 31 1 4-methyl- benzyl Glc(.beta.-D form) acetyl 50 cyclohexyl32 32 1 vinyl benzyl Glc(.beta.-D form) acetyl 5333 33 1 3-hexenyl benzyl Glc(.beta.-D form) acetyl 5734 34 1 geranyl benzyl Glc(.beta.-D form) acetyl 5435 35 1 C.sub.18 H.sub.17 benzyl Glc(.beta.-D form) benzyl 5736 36 1 benzyl H Glc(.beta.-D form) benzyl 5237 37 3 C.sub.4 H.sub.9 H Glc(.beta.-D form) H 8338 38 3 C.sub.6 H.sub.13 H Glc(.beta.-D form) H 8239 39 3 C.sub.8 H.sub.17 H Glc(.beta.-D form) H 8640 40 3 C.sub.10 H.sub.21 H Glc(.beta.-D form) H 7441 41 3 C.sub.12 H.sub.25 H Glc(.beta.-D form) H 8342 42 3 (CH.sub.3).sub.2 CH H Glc(.beta.-D form) H 8843 43 3 4-methyl- H Glc(.beta.-D form) H 81 cyclohexyl44 44 3 vinyl H Glc(.beta.-D form) H 8545 45 3 3-hexenyl H Glc(.beta.-D form) H 8646 46 3 geranyl H Glc(.beta.-D form) H 8347 47 3 benzyl H Glc(.beta.-D form) H 8748 48 4 CH.sub.3 benzyl Man(.alpha.-D form) benzyl 5349 49 4 C.sub.4 H.sub.9 benzyl Man(.alpha.-D form) benzyl 5150 50 4 C.sub.6 H.sub.13 benzyl Man(.alpha.-D form) acetyl 5451 51 4 C.sub.8 H.sub.17 benzyl Man(.alpha.-D form) acetyl 5652 52 4 C.sub.10 H.sub.21 benzyl Man(.alpha.-D form) acetyl 5953 53 4 C.sub.12 H.sub.25 benzyl Man(.alpha.-D form) acetyl 5554 54 4 (CH3)2CH benzyl Man(.alpha.-D form) acetyl 5555 55 4 4-methyl- benzyl Man(.alpha.-D form) acetyl 53 cyclohexyl56 56 4 vinyl benzyl Man(.alpha.-D form) acetyl 5557 57 4 3-hexenyl benzyl Man(.alpha.-D form) acetyl 5958 58 4 geranyl benzyl Man(.alpha.-D form) acetyl 5759 59 4 C.sub.8 H.sub.17 benzyl Man(.alpha.-D form) benzyl 5060 60 4 benzyl benzyl Man(.alpha.-D form) benzyl 5061 61 6 H H Man(.alpha.-D form) H 8962 62 6 C.sub.4 H.sub.9 H Man(.alpha.-D form) H 8063 63 6 C.sub.6 H.sub.13 H Man(.alpha.-D form) H 7964 64 6 C.sub.8 H.sub.17 H Man(.alpha.-D form) H 8665 65 6 C.sub.10 H.sub.21 H Man(.alpha.-D form) H 7966 66 6 C.sub.12 H.sub.25 H Man(.alpha.-D form) H 8067 67 6 (CH.sub.3).sub.2 CH H Man(.alpha.-D form) H 7968 68 6 4-methyl- H Man(.alpha.-D form) H 81 cyclohexyl69 69 6 vinyl H Man(.alpha.-D form) H 7970 70 6 3-hexenyl H Man(.alpha.-D form) H 8971 71 6 geranyl H Man(.alpha.-D form) H 8072 72 6 benzyl H Man(.alpha.-D form) H 9073 73 7 CH.sub.3 benzyl Gal(.beta.-D form) benzyl 5874 74 7 C.sub.4 H.sub.9 benzyl Gal(.beta.-D form) benzyl 6075 75 7 C.sub.6 H.sub.13 benzyl Gal(.beta.-D form) acetyl 5776 76 7 C.sub.8 H.sub.17 benzyl Gal(.beta.-D form) acetyl 5877 77 7 C.sub.10 H.sub.21 benzyl Gal(.beta.-D form) acetyl 5878 78 7 C.sub.12 H.sub.25 benzyl Gal(.beta.-D form) acetyl 5579 79 7 (CH.sub.3).sub.2 CH benzyl Gal(.beta.-D form) acetyl 5980 80 7 4-methyl- benzyl Gal(.beta.-D form) acetyl 57 cyclohexyl81 81 7 vinyl benzyl Gal(.beta.-D form) acetyl 6082 82 7 3-hexenyl benzyl Gal(.beta.-D form) acetyl 5883 83 7 geranyl benzyl Gal(.beta.-D form) benzyl 6084 84 7 C.sub.8 H.sub.17 benzyl Gal(.beta.-D form) benzyl 5985 85 7 benzyl benzyl Gal(.beta.-D form) H 5986 86 9 C.sub.4 H.sub.9 H Gal(.beta.-D form) H 8687 87 9 C.sub.6 H.sub.13 H Gal(.beta.-D form) H 8988 88 9 C.sub.8 H.sub.17 H Gal(.beta.-D form) H 9089 89 9 C.sub.10 H.sub.21 H Gal(.beta.-D form) H 7890 90 9 C.sub.12 H.sub.25 H Gal(.beta.-D form) H 7991 91 9 (CH.sub.3).sub.2 CH H Gal(.beta.-D form) H 9092 92 9 4-methyl- H Gal(.beta.-D form) H 82 cyclohexyl93 93 9 vinyl H Gal(.beta.-D form) H 8194 94 9 3-hexenyl H Gal(.beta.-D form) H 7895 95 9 geranyl H Gal(.beta.-D form) H 7696 96 9 benzyl H Gal(.beta.-D form) H 6997 97 13 acetyl H Glc(.beta.-D form) acetyl 5898 98 13 acetyl CH.sub.3 Glc(.beta.-D form) acetyl 5699 99 13 propionyl C.sub.4 H.sub.9 Glc(.beta.-D form) acetyl 48100 100 13 propionyl C.sub.10 H.sub.21 Glc(.beta.-D form) benzyl 65101 101 13 propionyl C.sub.12 H.sub.25 Glc(.beta.-D form) benzyl 71102 102 13 acetyl (CH3)2CH Glc(.beta.-D form) benzyl 72103 103 13 acetyl 4-methyl- Glc(.beta.-D form) acetyl 68 cyclohexy104 104 13 acetyl vinyl Glc(.beta.-D form) acetyl 68105 105 13 acetyl 3-hexenyl Glc(.beta.-D form) acetyl 69106 106 13 butyryl geranyl Glc(.beta.-D form) acetyl 58107 107 13 butyryl benzyl Glc(.beta.-D form) benzyl 68108 108 19 H H Glc(.beta.-D form) H 85109 109 19 H CH.sub.3 Glc(.beta.-D form) H 81110 110 19 H C.sub.4 H.sub.9 Glc(.beta.-D form) H 78111 111 19 H C.sub.10 H.sub.21 Glc(.beta.-D form) H 79112 112 19 H C.sub.12 H.sub.25 Glc(.beta.-D form) H 81113 113 19 H (CH.sub.3).sub.2 CH Glc(.beta.-D form) H 89114 114 19 H 4-methyl- Glc(.beta.-D form) H 78 H cyclohexy115 115 19 H vinyl Glc(.beta.-D form) H 81116 116 19 H 3-hexenyl Glc(.beta.-D form) H 82117 117 19 H geranyl Glc(.beta.-D form) H 81118 118 19 H benzyl Glc(.beta.-D form) H 85119 119 14 acetyl H Man(.alpha.-D form acetyl 62120 120 14 acetyl CH.sub.3 Man(.alpha.-D form acetyl 58121 121 14 propionyl C.sub.8 H.sub.17 Man(.alpha.-D form benzyl 58122 122 14 propionyl C.sub.10 H.sub.21 Man(.alpha.-D form benzyl 56123 123 14 propionyl C.sub.12 H.sub.25 Man(.alpha.-D form benzyl 68124 124 14 acetyl (CH.sub.3).sub.2 CH Man(.alpha.-D form benzyl 61125 125 14 acetyl 4-methyl- Man(.alpha.-D form acetyl 69 cyclohexy126 126 14 acetyl vinyl Man(.alpha.-D form acetyl 70127 127 14 acetyl 3-hexenyl Man(.alpha.-D form acetyl 69128 128 14 butyryl geranyl Man(.alpha.-D form acetyl 65129 129 14 butyryl benzyl Man(.alpha.-D form benzyl 68130 130 20 H H Man(.alpha.-D form H 85131 131 20 H CH.sub.3 Man(.alpha.-D form H 81132 132 20 H C.sub.8 H.sub.17 Man(.alpha.-D form H 78133 133 20 H C.sub.10 H.sub.21 Man(.alpha.-D form H 76134 134 20 H C.sub.12 H.sub.25 Man(.alpha.-D form H 79135 135 20 H (CH.sub.3).sub.2 CH Man(.alpha.-D form H 74136 136 20 H 4-methyl- Man(.alpha.-D form H 68 H cyclohexy137 137 20 H vinyl Man(.alpha.-D form H 79138 138 20 H 3-hexenyl Man(.alpha.-D form H 81139 139 20 H geranyl Man(.alpha.-D form H 71140 140 20 H benzyl Man(.alpha.-D form H 83141 141 12 acetyl H Glc(.beta.-D form) acetyl 62142 142 12 acetyl CH.sub.3 Glc(.beta.-D form) acetyl 62143 143 12 propionyl C.sub.10 H.sub.21 Glc(.beta.-D form) benzyl 59144 144 12 propionyl C.sub.12 H.sub.25 Glc(.beta.-D form) benzyl 68145 145 12 acetyl (CH.sub.3).sub.2 CH Glc(.beta.-D form) benzyl 71146 146 12 acetyl 4-methyl- Glc(.beta.-D form) acetyl 68 cyclohexy147 147 12 acetyl vinyl Glc(.beta.-D form) acetyl 70148 148 12 acetyl 3-hexenyl Glc(.beta.-D form) acetyl 69149 149 12 butyryl geranyl Glc(.beta.-D form) acetyl 69150 150 12 butyryl benzyl Glc(.beta.-D form) benzyl 59151 151 21 H H Glc(.beta.-D form) H 80152 152 21 H benzyl Glc(.beta.-D form) H 76153 153 21 H CH.sub.3 Glc(.beta.-D form) H 83154 154 21 H C.sub.10 H.sub.21 Glc(.beta.-D form) H 81155 155 21 H C.sub.12 H.sub.25 Glc(.beta.-D form) H 68156 156 21 H (CH.sub.3).sub.2 CH Glc(.beta.-D form) H 72157 157 21 H 4-methyl- Glc(.beta.-D form) H 78 H cyclohexy158 158 21 H vinyl Glc(.beta.-D form) H 68159 159 21 H 3-hexenyl Glc(.beta.-D form) H 69160 160 21 H geranyl Glc(.beta.-D form) H 79__________________________________________________________________________ Compound 24

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 25H), 6.88 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.42 (s, 2H), 5.35.about.5.25 (m, 2H), 5.20 (m, 8H), 5.12 (t, 1H, J=8.0 Hz), 4.95 (d, 1H,J=8.0 Hz), 4.30.about.4.20 (m, 2H), 3.85.about.3.81 (m, 1H), 3.73 (s, 3H)

IR (KBr, cm.sup.-1): 1645, 1600, 1440, 1380

Elemental analysis for C.sub.51 H.sub.48 O.sub.10 Calculated (%): C 74.62;H 5.89;O 19.49 Found (%):C 74.53;H 5.88;O 19.59

Compound 25

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.15 (m, 25H), 6.88 (d, 1H, J=8.8 Hz), 6.82 (s, 1H), 5.42 (s, 2H), 5.35.about.5.25 (m, 2H), 5.22 (m, 8H), 5.17 (t, 1H, J=8.0 Hz), 4.93 (d, 1H, J=8.0 Hz), 4.40 (t, 2H, J=6.8 Hz), 4.30.about.4.21 (m, 2H), 3.85.about.3.81(m, 1H), 1.75.about.1.24 (m, 4H), 0.93 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1645, 1610, 1435, 1380

Elemental analysis for C.sub.54 H.sub.54 O.sub.10 Calculated (%): C 75.15;H 6.31;O 18.54 Found (%): C 75.23;H 6.28;O 18.49

Compound 26

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.71 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.88 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.42 (s, 2H), 5.35.about.5.25 (m, 2H), 5.10 (t, 1H, J=8.0 Hz), 4.95 (d, 1H, J=8.0 Hz), 4.52 (t, 2H, J=6.5 Hz), 4.30.about.4.20 (m, 2H), 3.85.about.3.80 (m, 1H), 2.20.about.2.00 (m, 12H), 1.78.about.1.28 (m, 8H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1765, 1645, 1610, 1440, 1380

Elemental analysis for C.sub.36 H.sub.42 O.sub.14 Calculated (%): C 61.89;H 6.06;O 32.05 Found (%): C 61.73;H 6.18;O 32.09

Compound 27

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.62.about.7.20 (m, 5H), 6.90 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 5.42 (s, 2H), 5.35.about.5.25 (m, 2H), 5.10 (t, 1H, J=8.0 Hz), 4.98 (d, 1H, J=8.0 Hz), 4.50 (t, 2H, J=6.5 Hz), 4.28.about.4.20 (m, 2H), 3.84 .ANG.3.80 (m, 1H), 2.20.about.1.98 (m, 12H), 180.about.1.25 (m, 12H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1765, 1645, 1600, 1445, 1380

Elemental analysis for C.sub.38 H.sub.46 O.sub.14 Calculated (%): C 62.80;H 6.38;O 30.82 Found (%): .ANG.FC 62.83;H 6.43;O 30.74

Compound 28

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.88 (d, 1H, J=8.8 Hz), 6.79 (s, 1H), 5.42 (s, 2H), 5.35.about.5.25 (m, 2H), 5.08 (t, 1H, J=8.0 Hz), 4.97 (d, 1H, J=8.0 Hz), 4.52 (t, 2H, J=6.5 Hz), 4.30.about.4.18 (m, 2H), 3.85.about.3.80 (m, 1H), 2.22.about.2.00 (m, 12H), 180.about.1.20 (m, 16H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1760, 1645, 1610, 1430, 1380

Elemental analysis for C.sub.40 H.sub.50 O.sub.14 Calculated (%): C 63.65;H 6.68;O 29.67 Found (%): C 63.53;H 6.78;O 29.69

Compound 29

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.73 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.42 (s, 2H), 5.35.about.5.25 (m, 2H), 5.12 (t, 1H, J=8.0 Hz), 4.95 (d, 1H, J=8.0 Hz), 4.52 (t, 2H, J=6.5 Hz), 4.27.about.4.18 (m, 2H), 3.85.about.3.80 (m, 1H), 2.20.about.2.00 (m, 12H), 1.83.about.1.25 (m, 20H), 0.90 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1765, 1640, 1605, 1440, 1380

Elemental analysis for C.sub.42 H.sub.43 O.sub.14 Calculated (%): C 64.44;H 6.95;O 28.61 Found (%): C 64.53;H 6.78;O 28.69

Compound 30

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.74 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 5.42 (s, 2H), 5.35.about.5.23 (m, 2H), 5.12 (t, 1H, J=8.0 Hz), 4.97 (d, 1H, J=8.0 Hz), 4.51 (m, 1H), 4.26.about.4.16 (m, 2H), 3.83.about.3.78 (m, 1H), 2.22.about.2.00 (m, 12H), 1.03 (d, 6H, J=7.4 Hz)

IR (KBr, cm.sup.-1): 1770, 1650, 1605, 1435, 1380

Elemental analysis for C.sub.33 H.sub.36 O.sub.14 Calculated (%): C 60.36;H 5.53;O 34.11 Found (%): C 60.33;H 5.68;O 33.99

Compound 31

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.60.about.7.18 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.44 (s, 2H), 5.32.about.5.24 (m, 2H), 5.12 (t, 1H, J=8.0 Hz), 5.00 (m, 1H), 4.95 (d, 1H, J=8.0 Hz), 4.28.about.4.18 (m, 2H), 3.84.about.3.80 (m, 1H), 2.23.about.1.26 (m, 21H), 0.96 (d, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 1760, 1640, 1605, 1445, 1380

Elemental analysis for C.sub.37 H.sub.42 O.sub.14 Calculated (%): C 62.53;H 5.96;O 31.51 Found (%): C 62.83;H 5.75;O 31.42

Compound 32

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.72 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.87 (d, 1H, J=8.8 Hz), 6.75 (s, 1H), 6.44 (dd, 1H, J=17.5 Hz, J=9.4 Hz), 5.42 (s, 2H), 5.34.about.5.24 (m, 2H), 5.12 (t, 1H, J=8.0 Hz), 4.95 (d, 1H, J=8.0 Hz), 4.28.about.4.16 (m, 2H), 4.13 (dd, 1H, J=17.6 Hz, J=2.0 Hz), 3.91 (dd, 1H, J=9.4 Hz, J=1.9Hz), 3.85.about.3.79(m, 1H), 2.19.about.2.00 (m, 12H)

IR (KBr, cm.sup.-1): 1765, 1635, 1600, 1440, 1375

Elemental analysis for C.sub.32 H.sub.32 O.sub.14 Calculated (%): C 60.00;H 5.04;O 34.96 Found (%): C 59.93;H 5.08;O 34.99

Compound 33

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.71 (d, 1H, J=8.8 Hz), 7.58.about.7.20 (m, 5H), 6.86 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 5.42 (s, 2H), 5.35.about.5.25 (m, 4H), 5.10 (t, 1H, J=8.0 Hz), 4.97 (d, 1H, J=8.0 Hz), 4.28.about.4.22 (m, 4H), 3.86.about.3.81 (m, 1H), 2.30.about.1.94 (m, 16H),0.98 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 1765, 1650, 610, 1440, 1370

Elemental analysis for C.sub.36 H.sub.40 O.sub.14 Calculated (%): C 62.06;H 5.79;O 32.15 Found (%): C 62.13;H 5.78;O 32.09

Compound 34

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.74 (d, 1H, J=8.8 Hz), 7.62.about.7.22 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.76 (s, 1H), 5.42 (s, 2H), 5.36.about.5.26 (m, 3H), 5.10 (m, 2H), 4.95 (d, 1H, J=8.0 Hz), 4.27.about.4.17(m, 2H), 4.12 (d, 2H, J=8.6 Hz), 3.86.about.3.80 (m, 1H), 2.19.about.1.98(m, 16H), 1.68 (s, 6H), 1.59 (s, 3H)

IR (KBr, cm.sup.-1): 1760, 1645, 1605, 1440, 1370

Elemental analysis for C.sub.40 H.sub.46 O.sub.14 Calculated (%): C 63.99;H 6.18;O 29.83 Found (%): C 63.83;H 6.24;O) 29.93

Compound 35

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.67 (d, 1H, J=8.8 Hz), 7.55.about.7.15 (m, 25H), 6.73 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 5.58 (s, 2H), 5.37.about.5.24 (m, 2H), 5.15 (m, 8H), 5.10 (t, 1H, J=8.0 Hz), 4.96 (d, 1H, J=8.0 Hz), 4.51 (t, 2H, J=6.8 Hz), 4.24.about.4.19 (m, 2H), 3.86.about.3.82 (m, 1H), 1.77.about.1.20 (m, 12H), 0.91 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1645, 1610, 1440, 1380

Elemental analysis for C.sub.58 H.sub.62 O.sub.10 Calculated (%): C 75.79;H 6.80;O 17.41 Found (%): C 75.83;H 6.78;O 17.39

Compound 36

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.70.about.7.15 (m, 30H), 6.90 (d, 1H, J=8.8 Hz), 6.79 (s, 1H), 5.45 (s, 2H), 5.35.about.5.25 (m, 2H), 5.17 (m, 10H), 5.08 (t, 1H, J=8.0 Hz), 4.90 (d, 1H, J=8.0 Hz), 4.29.about.4.21 (m, 2H), 3.87.about.3.78 (m, 1H)

IR (KBr, cm.sup.-1): 1640, 1605, 1445, 1370

Elemental analysis for C.sub.57 H.sub.52 O.sub.10 Calculated (%): C 76.32;H 5.84;O 17.84 Found (%): C 76.53;H 5.78;O 17.69

Compound 37

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.32 (bs, 1H), 7.59 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.39 (bs, 1H), 5.11 (bs, 1H), 5.06 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.60 (bs, 1H), 4.25 (t, 2H, J=6.2 Hz), 3.76.about.3.10 (m, 6H), 180.about.1.20 (m, 4H), 0.88 (t, 3H), J=7.0 Hz)

IR (KBr, cm.sup.-1): 3350, 2960, 2920, 2840, 1700, 1645, 1610, 1260

Elemental analysis for C.sub.19 H.sub.24 O.sub.10 Calculated (%): C 55.33;H 5.87;O 38.80 Found (%): C 55.29;H 5.89;O 38.82

Compound 38

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.45 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.11.about.7.02 (m, 2H), 5.35 (bs, 1H), 5.09 (bs, 1H), 5.04 (bs, 1H), 4.95 (d, 1H, J=7.2 Hz), 4.57 (bs, 1H), 4.42 (t, 2H, J=6.4 Hz), 3.82.about.3.12 (m, 6H), 1.80.about.1.20 (m, 8H), 0.85 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3345, 2920, 2850, 1710, 1635, 1610, 1250

Elemental analysis for C.sub.21 H.sub.28 O.sub.10 Calculated (%): C 57.26;H 6.41;O 36.33 Found (%): C 57.20;H 6.35;O 36.45

Compound 39

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.40 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.12.about.7.02 (m, 2H), 5.37 (bs, 1H), 5.10 (bs, 1H), 5.04 (bs, 1H), 4.95 (d, 1H, J=7.2 Hz), 4.56 (bs, 1H), 4.41 (t, 2H, J=6.4 Hz), 3.80.about.3.12 (m, 6H), 1.82.about.1.13 (m, 12H), 0.85 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3350, 2920, 2845, 1700, 1635, 1610, 1250

Elemental analysis for C.sub.23 H.sub.32 O.sub.10 Calculated (%):C 58.96;H 6.89;O 34.15 Found (%): C 59.06;H 6.77;O 34.17

Compound 40

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.20 (bs, 1H), 7.62 (d, 1H, J=8.8 Hz), 7.12.about.7.02 (m, 2H), 5.33 (bs, 1H), 5.12 (bs, 1H), 5.04 (bs, 1H), 4.95 (d, 1H, J=7.2 Hz), 4.56 (bs, 1H), 4.38 (t, 2H, J=6.4 Hz), 3.75.about.3.10 (m, 6H), 1.85.about.1.15 (m, 16H), 0.85 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3340, 2925, 2845, 1705, 1650, 1620, 1250

Elemental analysis for C.sub.23 H.sub.32 O.sub.10 Calculated (%): C 60.47;H 7.31;O 32.22 Found (%): C 60.45;H 7.35;O 32.20

Compound 41

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.45 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.39 (bs, 1H), 5.13 (bs, 1H), 5.05 (bs, 1H), 4.95 (d, 1H, J=7.2 Hz), 4.57 (bs, 1H), 4.25 (t, 2H, J=6.4 Hz), 3.80.about.3.18 (m, 6H), 180.about.1.60 (m, 2H), 1.52.about.1.12 (m, 18H), 0.88 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3350, 2910, 2850, 1700, 1650, 1610, 1250

Elemental analysis for C.sub.27 H.sub.40 O.sub.10 Calculated (%): C 61.81;H 7.69;O 30.50 Found (%): C 61.77;H 7.55;O 30.68

Compound 42

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.43 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.35 (bs, 1H), 5.10 (bs, 1H), 5.05 (bs, 1H), 4.99 (d, 1H, J=6.8 Hz), 4.62 (bs, 1H), 4.45 (m, 1H), 3.75.about.3.10 (m, 6H), 1.05 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 3330, 3300, 2940, 2850, 1700, 1600, 1250

Elemental analysis for C.sub.18 H.sub.22 O.sub.10 Calculated (%): C 54.27;H 5.57;O 40.16 Found (%): C 54.28;H 5.69;O 40.03

Compound 43

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 10.38 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.01 (m, 2H), 5.35 (bs, 1H), 5.10 (bs, 1H), 5.03 (bs, 1H), 4.98 (m, 1H), 4.93 (d, 1H, J=6.8 Hz), 4.53 (bs, 1H), 3.80.about.3.09 (m, 6H), 2.00.about.1.22 (m, 9H), 0.95 (d, 3H, J=6.5 Hz)

IR (KBr, cm.sup.-1): 3335, 3300, 2955, 2850, 1710, 1620, 1250

Elemental analysis for C.sub.22 H.sub.28 O.sub.10 Calculated (%):C 58.40;H 6.24;O 35.36 Found (%): C 58.35;H 6.29;O 35.36

Compound 44

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.48 (bs, 1H), 7.65 (d, 1H, J=8.8 Hz), 7.13.about.7.03 (m, 2H), 6.57 (dd, 1H, J=17.5 Hz, J=9.5 Hz), 5.35 (bs, 1H ), 5.15 (bs, 1H), 5.08 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.17 (dd, 1H, J=17.5 Hz, J=2.0 Hz), 3.95 (dd, 1H, J=9.5 Hz, J=2.0 Hz), 3.80.about.3.12 (m, 6H)

IR (KBr, cm.sup.-1): 3340, 3310, 2950, 2845, 1700, 1610, 1250

Elemental analysis for C.sub.17 H.sub.18 O.sub.10 Calculated (%): C 53.40;H 4.75;O 41.85 Found (%): C 53.57;H 4.69;O 41.74

Compound 45

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.40 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.50 (m, 1H), 5.34 (m, 2H), 5.11 (bs, 1H), 5.03 (bs, 1H), 4.98 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.27 (t, 2H, J=6.2 Hz), 3.83.about.3.15 (m, 6H), 2.25.about.1.96 (m, 4H), 0.99 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 1710, 1640, 1615, 1260

Elemental analysis for C.sub.21 H.sub.26 O.sub.10 Calculated (%): C 57.53;H 5.98;O 36.49 Found (%): C 57.65;H 5.89;O 36.46

Compound 46

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.35 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12.about.7.00 (m, 2H), 5.38 (m, 1H), 5.34 (bs, 1H), 5.10 (m, 2H), 5.05 (bs, 1H), 4.98 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.10 (d,2H, J=8.5 Hz), 3.80.about.3.15 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s, 3H)

IR (KBr, cm.sup.-1): 3345, 2950, 2920, 1705, 1640, 1610, 1260

Elemental analysis for C.sub.25 H.sub.32 O.sub.10 Calculated (%):C 60.96;H 6.55;O 32.49 Found (%): C 60.85;H 6.70;O 32.45

Compound 47

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.50 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz),7.30.about.7.15 (m, 5H), 7.10.about.7.00 (m, 2H), 5.35 (bs, 1H), 5.25 (s,2H), 5.11 (bs, 1H), 5.00 (bs, 1H), 4.93 (d, 1H, J=6.8 Hz), 4.55(bs, 1H), 3.80.about.3.10 (m, 6H)

IR (KBr, cm.sup.-1): 3340, 3300, 2955, 2850, 1710, 1620, 1260

Elemental analysis for C.sub.22 H.sub.22 O.sub.10 Calculated (%): C 59.19;H 4.97;O 35.84 Found (%): C 59.15;H 4.89;O 35.96

Compound 48

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.71 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m,25H), 6.88 (d, 1H, J=8.8 Hz), 6.75 (s, 1H), 6.00 (S, 1H), 5.54(m, 2H), 5.43 (s, 2H), 5.39 (m, 1H), 5.20 (m, 8H),4.24 (m, 2H),4.15 (s, 1H), 3.73 (s, 3H)

IR (KBr, cm.sup.-1): 1645, 1610, 1440, 1380

Elemental analysis for C.sub.51 H.sub.48 O.sub.10 Calculated (%): C 74.62;H 5.89;O 19.49 Found (%): C 74.56;H 5.84;O 19.60

Compound 49

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.15 (m,25H), 6.88 (d, 1H, J=8.8 Hz), 6.75 (s, 1H), 6.00 (S, 1H), 5.55(s, 2H), 5.42 (s, 2H), 5.40 (m, 1H), 5.22 (m, 8H), 4.42 (t, 2H, J=6.7 Hz), 4.25 (m, 2H), 4.15 (s, 1H), 1.75.about.1.24 (m, 4H), 0.93 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1645, 1610, 1435, 1380

Elemental analysis for C.sub.54 H.sub.54 O.sub.10 Calculated (%): C 75.15;H 6.31;O 18.54 Found (%): C 75.23;H 6.28;O 18.49

Compound 50

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m,5H), 6.88 (d, 1H, J=8.8 Hz), 6.79 (s, 1H), 6.02 (s, 1H), 5.56 (m,2H), 5.42 (s, 2H), 5.40 (m, 1H), 4.50 (t, 2H, J=6.5 Hz), 4.24 (m, 2H), 4.15 (s, 1H), 2.18.about.1.98 (m, 12H), 1.80.about.1.30 (m, 8H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1765, 1645, 1610, 1435, 1380

Elemental analysis for C.sub.36 H.sub.42 O.sub.14 Calculated (%): C 61.89;H 6.06;O 32.05 Found (%): C 61.74;H 6.10;O 32.06

Compound 51

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.62.about.7.20 (m, 5H), 6.90 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.02 (s, 1H), 5.56 (m, 2H), 5.44 (s, 2H), 5.41 (m, 1H), 4.50 (t, 2H, J=6.5 Hz), 4.25 (m, 2H), 4.13 (s, 1H), 2.20.about.1.98 (m, 12H), 1.80.about.1.25 (m, 12H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1760, 1640, 1600, 1445, 1380

Elemental analysis for C.sub.38 H.sub.46 O.sub.14 Calculated (%): C 62.80;H 6.38;O 30.82 Found (%): C 62.87;H 6.33;O 30.80

Compound 52

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.88 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.03 (s, 1H), 5.57 (m, 2H), 5.42 (s, 2H), 5.40 (m, 1H), 4.52 (t, 2H, J=6.5 Hz), 4.25 (m, 2H), 4.13 (s, 1H), 2.23.about.2.00 (m, 12H), 1.81.about.1.21 (m, 16H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1760, 1635, 1600, 1430, 1380

Elemental analysis for C.sub.40 H.sub.50 O.sub.14 Calculated (%):C 63.65;H 6.68;O 29.67 Found (%): C 63.63;H 6.85;O 29.52

Compound 53

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.43 (s, 2H), 5.38 (m, 1H), 4.51 (t, 2H, J=6.5 Hz), 4.23 (m, 2H), 4.12 (s, 1H), 2.20.about.2.02 (m, 12H), 1.84.about.1.24 (m, 20H),0.90 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1760, 1640, 1610, 1440, 1380

Elemental analysis for C.sub.42 H.sub.54 O.sub.14 Calculated (%): C 64.44;H 6.95;O 28.61 Found (%):C 64.47;H 6.88;O 28.65

Compound 54

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.71 (d, 1H, J=8.8 Hz), 7.56.about.7.17 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.00 (s, 1H), 5.59 (m, 2H), 5.42 (s, 2H), 5.39 (m, 1H), 4.50 (m, 1H), 4.23 (m, 2H), 4.12 (s, 1H), 2.22.about.2.00 (m, 12H), 1.05 (d, 6H, J=7.4 Hz)

IR (KBr, cm.sup.-1): 1770, 1645, 1605, 1430, 1380

Elemental analysis for C.sub.33 H.sub.36 O.sub.14 Calculated (%): C 60.36;H 5.53;O 34.11 Found (%): C 60.39;H 5.64;O 33.97

Compound 55

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.72 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.44 (s, 2H), 5.41 (m, 1H), 5.00 (m, 1H), 4.22 (m, 2H), 4.13 (s, 1H), 2.23.about.1.26 (m, 21H), 0.96 (d, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 1750, 1640, 1600, 1445, 1380

Elemental analysis for C.sub.37 H.sub.42 O.sub.14 Calculated (%):C 62.53;H 5.96;O 31.51 Found (%): C 62.63;H 5.85;O 31.52

Compound 56

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.73 (d, 1H, J=8.8 Hz), 7.59.about.7.18 (m, 5H), 6.87 (d, 1H, J=8.8 Hz), 6.74 (s, 1H), 6.44 (dd, 1H, J=17.5 Hz, J=9.4 Hz), 6.00 (s, 1H), 5.50 (m, 2H), 5.42 (s, 2H), 5.40 (m, 1H), 4.24 (m, 2H), 4.15 (s, 1H), 4.13 (dd, 1H, J=17.6 Hz, J=2.0 Hz), 3.91 (dd, 1H, J=9.4 Hz, J=1.9 Hz), 2.22.about.2.00 (m, 12H)

IR (KBr, cm.sup.-1): 1765, 1640, 1600, 1435, 1375

Elemental analysis for C.sub.32 H.sub.32 O.sub.14 Calculated (%):C 60.00;H 5.04;O 34.96 Found (%): C 59.97;H 5.10;O 34.93

Compound 57

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.58.about.7.20 (m,5H), 6.86 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 6.00 (s, 1H), 5.50 (m, 2H), 5.43 (s, 2H), 5.41 (m, 1H), 5.34 (m, 2H), 4.26 (t, 2H, J=6.2 Hz), 4.23 (m, 2H), 4.14 (s, 1H), 2.30.about.1.96 (m, 16H), 0.98 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 1760, 1650, 1610, 1440, 1370

Elemental analysis for C.sub.36 H.sub.40 O.sub.14 Calculated (%):C 62.06;H 5.79;O 32.15 Found (%): C 62.03;H 5.88;O 32.09

Compound 58

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.72 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.76 (s, 1H), 6.02 (s, 1H), 5.50 (m, 2H), 5.44 (s, 2H), 5.41 (m, 1H), 5.35 (m, 1H), 5.13 (m, 1H), 4.23 (m, 2H), 4.14 (s, 1H), 4.12 (d, 2H, J=8.6 Hz), 2.20.about.1.98 (m, 16H), 1.68 (s, 6H), 1.58 (s, 3H)

IR (KBr, cm.sup.-1): 1765, 1645, 1600, 1440, 1370

Elemental analysis for C.sub.40 H.sub.46 O.sub.14 Calculated (%): C 63.99;H 6.18;O 29.83 Found (%): C 63.88;H 6.23;O 29.89

Compound 59

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.69 (d, 1H, J=8.8 Hz), 7.55.about.7.15 (m, 25H), 6.73 (d, 1H, J=8.8 Hz), 6.81 (s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.40 (m, 1H), 5.36 (s, 2H), 5.15 (m, 8H), 4.49 (t, 2H, J=6.8 Hz), 4.23 (m, 2H), 4.14 (s, 1H), 180.about.1.20 (m, 12H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1650, 1610, 1435, 1380

Elemental analysis for C.sub.58 H.sub.62 O.sub.10 Calculated (%): C 75.79;H 6.80;O 17.41 Found (%): C 75.87;H 6.74;O 17.39

Compound 60

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.15 (m, 30H), 6.90 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.46 (s, 2H), 5.41 (m, 1H), 5.17 (m, 10H), 4.22 (m, 2H), 4.15 (s, 1H)

IR (KBr, cm.sup.-1): 1640, 1600, 1445, 1370

Elemental analysis for C.sub.57 H.sub.52 O.sub.10 Calculated (%):C 76.32;H 5.84;O 17.84 Found (%):C 76.56;H 5.79;O 17.65

Compound 61

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.13 (s, 1H), 9.20 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.15 (d, 1H, J=2.4 Hz), 7.10 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.09 (bs, 1H), 4.85 (bs, 1H), 4.80 (bs, 1H), 3.85 (s, 1H), 3.75.about.3.25 (m, 6H)

IR (KBr, cm.sup.-1): 3340, 2950, 2910, 2850, 1690, 1620, 1610, 1250

Elemental analysis for C.sub.15 H.sub.16 O.sub.10 Calculated (%): C 50.56;H 4.53;O 44.91 Found (%): C 50.42;H 4.58;O 45.00

Compound 62

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.35 (bs, 1H), 7.57 (d, 1H, J=8.8 Hz), 7.14 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.08 (bs, 1H), 4.90 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J=6.4 Hz), 3.87 (s, 1H), 3.78.about.3.20 (m, 6H), 1.75.about.1.20 (m, 4H), 0.86 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3345, 2950, 2900, 2850, 1690, 1635, 1600, 1250

Elemental analysis for C.sub.19 H.sub.24 O.sub.10 Calculated (%): C 55.33;H 5.87;O 38.80 Found (%): C 55.35;H 5.90;O 38.75

Compound 63

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.15 (bs, 1H), 7.56 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.09 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.05 (bs, 1H), 4.90 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J=6.4 Hz), 3.86 (s, 1H), 3.75.about.3.20 (m, 6H), 1.70.about.1.30 (m, 8H), 0.90 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3355, 2950, 2900, 2850, 1670, 1630, 1610, 1250

Elemental analysis for C.sub.21 H.sub.28 O.sub.10 Calculated (%): C 57.26;H 6.41;O 36.33 Found (%): C 57.35;H 6.35;O 36.30

Compound 64 .sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.25 (bs, 1H), 7.58 (d, 1H, J=8.8 Hz), 7.14 (d, 1H, J=2.4 Hz), 7.09 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.08 (bs, 1H), 4.89 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J=6.4 Hz), 3.87 (s, 1H), 3.76.about.3.23 (m, 6H), 180.about.1.30 (m, 12H), 0.87 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2910, 2850, 1680, 1635, 1610, 1250

Elemental analysis for C.sub.23 H.sub.32 O.sub.10 Calculated (%): C 58.96;H 6.89;O 34.15 Found (%): C 58.85;H 6.85;O 34.30

Compound 65

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.05 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.15 (d, 1H, J=2.4 Hz), 7.09 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.45 (s, 1H), 5.09 (bs, 1H), 4.85 (bs, 1H), 4.74 (bs, 1H), 4.42 (t, 2H, J=6.4 Hz), 3.85 (s, 1H), 3.80.about.3.25 (m, 6H), 1.75.about.1.20 (m, 16H), 0.88 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2940, 2920, 2850, 1680, 1630, 1610, 1245

Elemental analysis for C.sub.25 H.sub.36 O.sub.10 Calculated (%): C 60.47;H 7.31;O 32.22 Found (%): C 60.45;H 7.40;O 32.15

Compound 66

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.85 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.08 (bs, 1H), 4.90 (bs, 1H), 4.80 (bs, 1H), 4.42 (t, 2H, J=6.4 Hz), 3.88 (s, 1H), 3.70.about.3.15 (m, 6H), 1.95.about.1.20 (m, 20H), 0.85 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2915, 2850, 1685, 1630, 1600, 1250

Elemental analysis for C.sub.27 H.sub.40 O.sub.10 Calculated (%):C 61.81;H 7.69;O 30.50 Found (%): C 61.75;H 7.55;O 30.70

Compound 67

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.98 (bs, 1H), 7.63 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.08 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.87 (bs, 1H), 4.76 (bs, 1H), 4.43 (m, 1H), 3.88 (s, 1H), 3.78.about.3.12 (m, 6H), 1.07 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 3330, 2950, 2910, 2845, 1690, 1630, 1615, 1250

Elemental analysis for C.sub.18 H.sub.22 O.sub.10 Calculated (%): C 54.27;H 5.57;O 40.16 Found (%): C 54.18;H 5.65;O 40.17

Compound 68

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 10.00 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.89 (bs, 1H), 4.76 (bs, 1H), 3.75.about.3.25 (m, 6H), 2.25.about.1.20 (m, 9H), 0.97 (d, 3H, J=6.7 Hz)

IR (KBr, cm.sup.-1): 3335, 2940, 2920, 2855, 1690, 1625, 1610, 1250

Elemental analysis for C.sub.22 H.sub.28 O.sub.10 Calculated (%): C 58.40;H 6.24;O 35.36 Found (%): C 58.33;H 6.34;O 35.33

Compound 69

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.10 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.13 (d, 1H, J=2.4 Hz), 7.08 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 6.45 (dd, 1H, J=17.5 Hz, J=9.5 Hz), 5.50 (s, 1H), 5.10 (bs, 1H), 4.87 (bs, 1H), 4.77 (bs, 1H), 4.13 (dd, 1H, J=17.5 Hz, J=2.0 Hz), 3.95 (dd, 1H, J=9.5 Hz, J=2.0 Hz), 3.87 (s, 1H), 3.76.about.3.21 (m, 6H)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2840, 1695, 1630, 1610, 1250

Elemental analysis for C.sub.17 H.sub.18 O.sub.10 Calculated (%): C 53.40;H 4.75;O 41.85 Found (%): C 53.43;H 4.80;O 41.77

Compound 70

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.78 (bs, 1H), 7.58 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.54 (m, 1H), 5.35 (m.2H), 5.08 (bs, 1H), 4.85 (bs, 1H), 4.78 (bs, 1H), 4.27 (t, 2H, J=6.2 Hz), 3.88 (s, 1H), 3.70.about.3.25 (m, 6H), 2.25.about.1.90 (m, 4H), 0.99 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3340, 2950, 2910, 2850, 1685, 1630, 1615, 1250

Elemental analysis for C.sub.21 H.sub.26 O.sub.10 Calculated (%):C 57.53;H 5.98;O 36.49 Found (%): C 57.60;H 5.83;O 36.57

Compound 71

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.95 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.41 (m, 1H), 5.16 (m, 1H), 5.09 (bs, 1H), 4.87 (bs, 1H), 4.77 (bs, 1H), 4.10 (d, 2H J=8.5 Hz), 3.85 (s, 1H), 3.75.about.3.25 (m, 6H), 2.00 (m, 4H), 1.64 (s, 6H), 1.58 (s, 3H)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2845, 1690, 1620, 1600, 1250

Elemental analysis for C.sub.25 H.sub.32 O.sub.10 Calculated (%): C 60.96;H 6.55;O 32.49 Found (%): C 60.89;H 6.60;O 32.51

Compound 72

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.30 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.38 (m, 5H), 7.15 (d, 1H, J=2.4 Hz), 7.09 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.25 (s, 2H), 5.07 (bs, 1H), 4.90 (bs, 1H), 4.79 (bs, 1H), 3.85 (s, 1H), 3.76.about.3.20 (m, 6H)

IR (KBr, cm.sup.-1): 3335, 2960, 2930, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.22 H.sub.22 O.sub.10 Calculated (%): C 59.19;H 4.97;O 35.84 Found (%): C 59.25;H 4.89;O 35.86

Compound 73

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.71 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 25H), 6.88 (d, 1H, J=8.8 Hz), 6.75 (s, 1H), 6.00 (S, 1H), 5.54 (m, 2H), 5.43 (s, 2H), 5.39 (s, 1H), 5.25.about.5.15 (m, 9H), 4.20.about.4.11 (m, 2H), 3.73 (s, 3H)

IR (KBr, cm.sup.-1): 1645, 1610, 1440, 1380

Elemental analysis for C.sub.51 H.sub.48 O.sub.10 Calculated (%): C 74.62;H 5.89;O 19.49 Found (%):C 74.56;H 5.84;O 19.60

Compound 74

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.15 (m, 25H), 6.88 (d, 1H, J=8.8 Hz), 6.75 (s, 1H), 6.00 (S, 1H), 5.55 (s, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.26.about.5.16 (m, 9H), 4.42 (t, 2H, J=6.7 Hz), 4.22.about.4.09 (m, 2H), 1.75.about.1.24 (m, 4H), 0.93 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1645, 1610, 1435, 1380

Elemental analysis for C.sub.54 H.sub.54 O.sub.10 Calculated (%): C 75.15;H 6.31;O 18.54 Found (%): C 75.23;H 6.28;O 18.49

Compound 75

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.88 (d, 1H, J=8.8 Hz), 6.79 (s, 1H), 6.02 (s, 1H), 5.56 (m, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.24.about.5.16 (m, 1H), 4.50 (t, 2H, J=6.5 Hz), 4.20.about.4.08 (m, 2H), 2.18.about.1.98 (m, 12H), 180.about.1.30 (m, 8H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1765, 1645, 1610, 1435, 1380

Elemental analysis for C.sub.36 H.sub.42 O.sub.14 Calculated (%): C 61.89;H 6.06;O 32.05 Found (%): C 61.74;H 6.10;O 32.06

Compound 76

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.62.about.7.20 (m, 5H), 6.90 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.02 (s, 1H), 5.56 (m, 2H), 5.44 (s, 2H), 5.41 (s, 1H), 5.22.about.5.14 (m, 1H), 4.50 (t, 2H, J=6.5 Hz), 4.20.about.4.10 (m, 2H), 2.20.about.1.98 (m, 12H), 180.about.1.25 (m, 12H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1760, 1640, 1600, 1445, 1380

Elemental analysis for C.sub.38 H.sub.46 O.sub.14 Calculated (%): C 62.80;H 6.38;O 30.82 Found (%): C 62.87;H 6.33;O 30.80

Compound 77

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.88 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.03 (s, 1H), 5.57 (m, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.23.about.5.15 (m, 1H), 4.52 (t, 2H, J=6.5 Hz), 4.21.about.4.08 (m, 2H), 2.23.about.2.00 (m, 12H), 1.81.about.1.21 (m, 16H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1760, 1635, 1600, 1430, 1380

Elemental analysis for C.sub.40 H.sub.50 O.sub.14 Calculated (%): C 63.65;H 6.68;O 29.67 Found (%): C 63.63;H 6.85;O 29.52

Compound 78

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.43 (s, 2H), 5.38 (s, 1H), 5.22.about.5.13 (m, 1H), 4.51 (t, 2H, J=6.5 Hz), 4.20.about.4.09 (m, 2H), 2.20.about.2.02 (m, 12H), 1.84.about.1.24 (m, 20H), 0.90 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1760, 1640, 1610, 1440, 1380

Elemental analysis for C.sub.42 H.sub.54 O.sub.14 Calculated (%): C 64.44;H 6.95;O 28.61 Found (%): C 64.47;H 6.88;O 28.65

Compound 79

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.71 (d, 1H, J=8.8 Hz), 7.56.about.7.17 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.00 (s, 1H), 5.59 (m, 2H), 5.42 (s, 2H), 5.39 (s, 1H), 5.24.about.5.16 (m, 1H), 4.50 (m, 1H), 4.19.about.4.08 (m, 2H), 2.22.about.2.00 (m, 12H), 1.05 (d, 6H, J=7.4 Hz)

IR (KBr, cm.sup.-1): 1770, 1645, 1605, 1430, 1380

Elemental analysis for C.sub.33 H.sub.36 O.sub.14 Calculated (%): C 60.36;H 5.53;O 34.11 Found (%): C 60.39;H 5.64;O 33.97

Compound 80

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.72 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 6.02 (s, 1H), 5.60 (m, 2H), 5.44 (s, 2H), 5.41 (s, 1H), 5.23.about.5.14 (m, 1H), 5.00 (m, 1H), 4.21.about.4.09 (m, 2H), 2.23.about.1.26 (m, 21H), 0.96 (d, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 1750, 1640, 1600, 1445, 1380

Elemental analysis for C.sub.37 H.sub.42 O.sub.14 Calculated (%): C 62.53;H 5.96;O 31.51 Found (%): C 62.63;H 5.85;O 31.52

Compound 81

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.73 (d, 1H, J=8.8 Hz), 7.59.about.7.18 (m, 5H), 6.87 (d, 1H, J=8.8 Hz), 6.74 (s, 1H), 6.44 (dd, 1H, J=17.5 Hz, J=9.4 Hz), 6.00 (s, 1H), 5.50 (m, 2H), 5.42 (s, 2H), 5.40 (s, 1H), 5.23.about.5.15 (m, 1H), 4.20.about.4.10 (m, 2H), 4.13 (dd, 1H, J=17.6 Hz, J=2.0 Hz), 3.91 (dd, 1H, J=9.4 Hz, J=1.9 Hz), 2.22.about.2.00 (m, 12H)

IR (KBr, cm.sup.-1): 1765, 1640, 1600, 1435, 1375

Elemental analysis for C.sub.32 H.sub.32 O.sub.14 Calculated (%): C 60.00;H 5.04;O 34.96 Found (%):C 59.97;H 5.10;O 34.93

Compound 82

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.70 (d, 1H, J=8.8 Hz), 7.58.about.7.20 (m, 5H), 6.86 (d, 1H, J=8.8 Hz), 6.78 (s, 1H), 6.00 (s, 1H), 5.50 (m, 2H), 5.43 (s, 2H), 5.41 (s, 1H), 5.34 (m, 2H), 5.21.about.5.13 (m, 1H), 4.26 (t, 2H, J=6.2 Hz), 4.20.about.4.12 (m, 2H), 2.30.about.1.96 (m, 16H), 0.98 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 1760, 1650, 1610, 1440, 1370

Elemental analysis for C.sub.36 H.sub.40 O.sub.14 Calculated (%):C 62.06;H 5.79;O 32.15 Found (%): C 62.03;H 5.88;O 32.09

Compound 83

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.72 (d, 1H, J=8.8 Hz), 7.60.about.7.20 (m, 5H), 6.85 (d, 1H, J=8.8 Hz), 6.76 (s, 1H), 6.02 (s, 1H), 5.50 (m, 2H), 5.44 (s, 2H), 5.41 (s, 1H), 5.34 (m, 1H), 5.20.about.5.13 (m, 2H), 4.19.about.4.11 (m, 2H), 4.12 (d, 2H, J=8.6 Hz), 2.20.about.1.98 (m, 16H), 1.68 (s, 6H), 1.58 (s, 3H)

IR (KBr, cm.sup.-1): 1765, 1645, 1600, 1440, 1370

Elemental analysis for C.sub.40 H.sub.46 O.sub.14 Calculated (%): C 63.99;H 6.18;O 29.83 Found (%): C 63.88;H 6.23;O 29.89

Compound 84

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.69 (d, 1H, J=8.8 Hz), 7.55.about.7.15 (m, 25H), 6.73 (d, 1H, J=8.8 Hz), 6.81 (s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.40 (s, 1H), 5.36 (s, 2H), 5.22.about.5.14 (m, 9H), 4.49 (t, 2H, J=6.8 Hz), 4.18.about.4.10 (m, 2H), 180.about.1.20 (m, 12H), 0.89 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 1650, 1610, 1435, 1380

Elemental analysis for C.sub.58 H.sub.62 O.sub.10 Calculated (%): C 75.79;H 6.80;O 17.41 Found (%): C 75.87;H 6.74;O 17.39

Compound 85

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.68 (d, 1H, J=8.8 Hz), 7.60.about.7.15 (m, 30H), 6.90 (d, 1H, J=8.8 Hz), 6.80 (s, 1H), 6.01 (s, 1H), 5.49 (m, 2H), 5.46 (s, 2H), 5.41 (s, 1H), 5.22.about.5.15 (m, 11H), 4.18.about.4.09 (m, 2H)

IR (KBr, cm.sup.-1): 1640, 1600, 1445, 1370

Elemental analysis for C.sub.57 H.sub.52 O.sub.10 Calculated (%): C 76.32;H 5.84;O 17.84 Found (%): C 76.56;H 5.79;O 17.65

Compound 86

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.25 (bs, 1H), 7.60 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.22 (bs, 1H), 4.96 (d, 1H, J=7.6 Hz), 4.90 (bs, 1H), 4.68 (bs, 1H), 4.55 (bs, 1H), 4.50 (t, 2H, J=6.6 Hz), 3.64.about.3.24 (m, 6H), 1.75.about.1.20 (m, 4H), 0.88 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3400, 2940, 2900, 2840, 1670, 1635, 1610, 1250

Elemental analysis for C.sub.19 H.sub.24 O.sub.10 Calculated (%):C 55.33;H 5.87;O 38.80 Found (%): C 55.30;H 5.93;O 38.77

Compound 87

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.35 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.08.about.6.98 (m, 2H), 5.20 (bs, 1H), 4.97 (d, 1H, J=7.6 Hz), 4.90 (bs, 1H), 4.68 (bs, 1H), 4.54 (bs, 1H), 4.49 (t, 2H, J=6.6 Hz), 3.65.about.3.24 (m, 6H), 1.81.about.1.20 (m, 8H), 0.90 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3400, 2960, 2900, 2840, 1675, 1630, 1610, 1250

Elemental analysis for C.sub.21 H.sub.28 O.sub.10 Calculated (%): C 57.26;H 6.41;O 36.33 Found (%): C 57.40;H 6.40;O 36.20

Compound 88

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.10 (bs, 1H), 7.62 (d, 1H, J=9.6 Hz), 7.10.intg.7.00 (m, 2H), 5.20 (bs, 1H), 4.98 (d, 1H, J=7.6 Hz), 4.90(bs, 1H), 4.65 (bs, 1H), 4.52 (bs, 1H), 4.52 (t, 2H, J=6.6 Hz), 3.64.about.3.24 (m, 6H), 180.about.1.15 (m, 12H), 0.89 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3450, 2940, 2910, 2850, 1675, 1630, 1610, 1250

Elemental analysis for C.sub.23 H.sub.32 O.sub.10 Calculated (%):C 58.96;H 6.89;O 34.15 Found (%): C 58.90;H 6.93;O 34.17

Compound 89

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.15 (bs, 1H), 7.60 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.20 (bs, 1H), 4.95 (d, 1H, J=7.6 Hz), 4.90 (bs, 1H), 4.68 (bs, 1H), 4.52 (bs, 1H), 4.49 (t, 2H, J=6.6 Hz), 3.64.about.3.24 (m, 6H), 1.81.about.1.20 (m, 16H), 0.92 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3400, 2940, 2900, 2850, 1670, 1630, 1610, 1250

Elemental analysis for C.sub.25 H.sub.36 O.sub.10 Calculated (%):C 60.47;H 7.31;O 32.22 Found (%):C 60.40;H 7.40;O 32.20

Compound 90

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.20 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.01 (m, 2H), 5.24 (bs, 1H), 4.91 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.65 (bs, 1H), 4.50 (bs, 1H), 4.49 (t, 2H, J=6.6 Hz), 3.65.about.3.25 (m, 6H), 1.79.about.1.20 (m, 20H), 0.88 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2945, 2920, 2850, 1675, 1630, 1600, 1250

Elemental analysis for C.sub.27 H.sub.40 O.sub.10 Calculated (%):C 61.81;H 7.69;O 30.50 Found (%): C 61.75;H 7.50;O 30.75

Compound 91

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.30 (bs, 1H), 7.59 (d, 1H, J=9.6 Hz), 7.12.about.7.02 (m, 2H), 5.20 (bs, 1H), 4.93 (d, 1H, J=7.6 Hz), 4.85 (bs, 1H), 4.67 (bs, 1H), 4.49 (m, 2H), 3.65.about.3.25 (m, 6H), 1.04 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 3400, 2960, 2930, 2850, 1690, 1635, 1610, 1250

Elemental analysis for C.sub.18 H.sub.22 O.sub.10 Calculated (%): C 54.27;H 5.57;O 40.16 Found (%): C 54.17;H 5.57;O 40.26

Compound 92

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 10.40 (bs, 1H), 7.60 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.20 (bs, 1H), 5.03 (m, 1H), 4.90 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.66 (bs, 1H), 4.55 (bs, 1H), 3.63.about.3.23 (m, 6H), 2.19.about.1.13 (m, 9H), 0.95 (d, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3340, 2970, 2920, 2850, 1680, 1635, 1610, 1250

Elemental analysis for C.sub.22 H.sub.28 O.sub.10 Calculated (%):C 58.40;H 6.24;O 35.36 Found (%): C 58.35;H 6.30;O 35.35

Compound 93

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.85 (bs, 1H), 7.59 (d, 1H, J=9.6 Hz), 7.09.about.6.99 (m, 2H), 6.45 (dd, 1H, J=17.5 Hz, J=9.5 Hz), 5.20 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.68 (bs, 1H), 4.52 (bs, 1H), 4.15 (dd, 1H, J=17.5 Hz, J=2.0 Hz), 3.93 (dd, 1H, J=9.5 Hz, J=2.0 Hz), 3.64.about.3.24 (m, 6H),

IR (KBr, cm.sup.-1): 3360, 2950, 2900, 2850, 1670, 1630, 1610, 1250

Elemental analysis for C.sub.17 H.sub.18 O.sub.10 Calculated (%): C 53.40;H 4.75;O 41.85 Found (%): C 53.51;H 4.78;O 41.71

Compound 94

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.73 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.11.about.7.01 (m, 2H), 5.50 (m, 1H), 5.35 (m. 1H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.91 (bs, 1H), 4.67 (bs, 1H), 4.50 (bs, 1H), 4.27 (t, 2H, J=6.2 Hz), 3.65.about.3.25 (m, 6H), 2.33.about.1.97 (m, 4H), 0.99 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3340, 2950, 2920, 1710, 1630, 1605, 1260

Elemental analysis for C.sub.21 H.sub.26 O.sub.10 Calculated (%): C 57.53;H 5.98;O 36.49 Found (%): C 57.67;H 5.95;O 36.38

Compound 95

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.29 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.09.about.7.00 (m, 2H), 5.40 (m, 1H), 5.21 (bs, 1H), 5.11 (m, 1H), 4.94 (d, 1H, J=7.6 Hz), 4.86 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.15 (d, 2H, J=8.5 Hz), 3.66.about.3.26 (m, 6H), 2.01 (m, 4H),1.67 (s, 6H), 1.64 (s, 3H)

IR (KBr, cm.sup.-1): 3350, 2950, 2915, 1700, 1660, 1605, 1260

Elemental analysis for C.sub.25 H.sub.32 O.sub.10 Calculated (%):C 60.96;H 6.55;O 32.49 Found (%): C 60.93;H 6.62;O 32.45

Compound 96

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.13 (bs, 1H), 7.60 (d, 1H, J=9.6 Hz), 7.34 (m, 5H), 7.10.about.7.05 (m, 2H), 5.28 (s, 2H), 5.19 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.90 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 3.65.about.3.24 (m, 6H)

IR (KBr, cm.sup.-1): 3330, 3300, 2930, 2840, 1700, 1620, 1260

Elemental analysis for C.sub.22 H.sub.22 O.sub.10 Calculated (%): C 59.19;H 4.97;O 35.84 Found (%): C 59.28;H 4.85;O 35.87

Compound 97

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.55 (s, 1H), 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H

IR (KBr, cm.sup.-1): 3320, 2950, 1750, 1620, 1370, 1240

Elemental analysis for C.sub.25 H.sub.26 O.sub.15 Calculated (%): C 53.00;H 4.59;O 42.41 Found (%): C 52.95;H 4.55;O 42.50

Compound 98

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 3H), 4.15 (s, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.26 H.sub.28 O.sub.15 Calculated (%): C 53.79;H 4.83;O 41.38 Found (%): C 53.85;H 4.79;O 41.36

Compound 99

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.46 (t, 2H, J=6.0 Hz), 4.40.about.4.10 (m, 3H), 2.25 (q, 2H, J=7.2 Hz), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 180.about.1.70 (m, 2H), 1.55.about.1.40 (m, 2H), 1.05 (t, 3H, J=7.2 Hz), 0.93 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2950, 2920, 2850, 1730, 1640, 1610, 1260

Elemental analysis for C.sub.30 H.sub.36 O.sub.15 Calculated (%): C 56.60;H 5.66;O 37.74 Found (%):C 56.55;H 5.79;O 37.66

Compound 100

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.35.about.7.20 (m, 20H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.30.about.5.18 (m, 8H),5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.46 (t, 2H, J=6.0 Hz), 4.40.about.4.10 (m, 3H), 2.25 (q, 2H, J=7.2 Hz), 1.95.about.1.40 (m, 16H), 1.07 (t, 3H, J=7.2 Hz), 0.93 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2920, 2850, 1725, 1640, 1610, 1250

Elemental analysis for C.sub.56 H.sub.64 O.sub.11 Calculated (%): C 73.68;H 7.02;O 19.30 Found (%): C 73.65;H 7.05;O 19.30

Compound 101

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.40.about.7.20 (m, 20H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.30.about.5.18 (m, 8H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.46 (t, 2H, J=6.0 Hz), 4.40.about.4.10 (m, 3H), 2.05.about.1.40 (m, 20H), 1.05 (t, 3H, J=7.4 Hz), 0.93 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2920, 2850, 1700, 1640, 1610, 1250

Elemental analysis for C.sub.58 H.sub.68 O.sub.11 Calculated (%):C 74.04;H 7.23;O 18.73 Found (%): C 74.08;H 7.35;O 18.57

Compound 102

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.40.about.7.20 (m, 20H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.30.about.5.18 (m, 8H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 4H), 2.25 (s, 3H), 1.05 (d, J=7.5 Hz, 6H)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1610, 1250

Elemental analysis for C.sub.48 H.sub.48 O.sub.11 Calculated (%): C 72.00;H 6.00;O 22.00 Found (%): C 71.95;H 5.96;O 22.09

Compound 103

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.99 (m, 1H), 4.40.about.4.10 (m, 3H), 2.34 (s, 3H), 2.20.about.1.25 (m, 9H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.98 (d, 3H, J=6.4 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.32 H.sub.38 O.sub.15 Calculated (%): C 58.00, H 5.74;O 36.26 Found (%):C 57.95;H 5.79;O 36.26

Compound 104

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 77.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 6.45 (dd, 1H, J=17 Hz, J=9.5 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz),5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 4H), 3.95 (dd, 1H, J=9.5 Hz), J=2.0 Hz), 2.34 (s, 3H),2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1605, 1250

Elemental analysis for C.sub.27 H.sub.28 O.sub.15 Calculated (%): C 54.73;H 4.73;O 40.54 Found (%): C 54.85;H 4.69;O 40.46

Compound 105

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz) 5.34 (m, 2H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 5H), 2.34 (s, 3H), 2.30.about.1.95 (m, 4H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.97 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1720, 1610, 1250

Elemental analysis for C.sub.31 H.sub.36 O.sub.15 Calculated (%): C 57.41;H 5.56;O 37.03 Found (%): C 57.45;H 5.59;O 36.96

Compound 106

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz) 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.11 (m, 2H), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.22 (m, 3H), 4.10 (d, 2H, J=8.5 Hz), 2.30 (m, 4H), 2.05 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.85 (m, 2H), 1.67 (s, 6H), 1.60 (s, 3H), 1.55 (m, 2H), 1.05 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1620, 1260

Elemental analysis for C.sub.37 H.sub.47 O.sub.15 Calculated (%): C 60.82;H 6.30;O 32.88 Found (%): C 60.85;H 6.35;O 32.80

Compound 107

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.35.about.7.15 (m, 25H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.20.about.5.35 (m, 10H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.15 (m, 3H), 2.30 (t, 2H, J=6.8 Hz), 1.55 (m, 2H), 1.05 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1705, 1620, 1260

Elemental analysis for C.sub.54 H.sub.52 O.sub.11 Calculated (%):C 73.97;H 5.94;O 20.09 Found (%): C 73.95;H 5.96;O 20.09

Compound 108

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.45 (s, 1H, 9.19 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H),5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 3.75.about.3.10 (m, 6H)

IR (KBr, cm.sup.-1): 3330, 3300, 2950, 2850, 1700, 1600, 1260

Elemental analysis for C.sub.15 H.sub.16 O.sub.10 Calculated (%): C 50.56;H 4.53;O 44.91 Found (%): C 50.55;H 4.49;O 44.96

Compound 109

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.35 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.23 (s, 3H), 3.75.about.3.10 (m, 6H)

IR (KBr, cm.sup.-1): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental analysis for C.sub.16 H.sub.18 O.sub.10 Calculated (%): C 51.89;H 4.90;O 43.21 Found (%): C 51.85;H 4.79;O 43.36

Compound 110

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.25 (t, 2H, J=6.2 Hz), 3.75.about.3.10 (m, 6H), 180.about.1.20 (m, 4H), 0.85 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1700, 1640, 1610, 1260

Elemental analysis for C.sub.19 H.sub.24 O.sub.10 Calculated (%):C 55.33;H 5.87;O 38.80 Found (%): C 55.25;H 5.89;O 38.86

Compound 111

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.10 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.95 (d, 1H, J=7.2 Hz), 4.59 (bs, 1H), 4.40 (t, 2H, J=6.4 Hz), 3.75.about.3.10 (m, 6H), 1.80.about.1.60 (m, 2H), 1.52.about.1.15 (m, 14H), 0.85 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3350, 2920, 2850, 1700, 1640, 1610, 1250

Elemental analysis for C.sub.25 H.sub.36 O.sub.10 Calculated (%): C 60.47;H 7.31;O 32.22 Found (%): C 60.35;H 7.45;O 32.20

Compound 112

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.15 (bs, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.37 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.95 (d, 1H, J=7.2 Hz), 4.59 (bs, 1H), 4.25 (t, 2H, J=6.4 Hz), 3.75.about.3.10 (m, 6H), 180.about.1.60 (m, 2H), 1.52.about.1.12 (m, 18H), 0.85 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3350, 2920, 2850, 1700, 1640, 1610, 1250

Elemental analysis for C.sub.27 H.sub.40 O.sub.10 Calculated (%): C 61.81;H 7.69;O 30.50 Found (%): C 61.75;H 7.45;O 30.80

Compound 113

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.35 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.45 (m, 1H), 3.75.about.3.10 (m, 6H), 1.05 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental analysis for C.sub.18 H.sub.22 O.sub.10 Calculated (%): C 54.27;H 5.57;O 40.16 Found (%): C 54.18;H 5.69;O 40.13

Compound 114

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.35 (bs, 1H), 5.11 (bs, 1H), 5.05 (bs, 1H), 5.00 (m, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 3.75.about.3.10 (m, 6H), 2.02.about.1.20 (m, 9H), 0.98 (d, 3H, J=6.5 Hz)

IR (KBr, cm.sup.-1): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental analysis for C.sub.22 H.sub.28 O.sub.10 Calculated (%):C 58.40;H 6.24;O 35.36 Found (%):C 58.45;H 6.29;O 35.26

Compound 115

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.25 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 6.55 (dd, 1H, J=17.5 Hz, J=9.5 Hz), 5.35 (bs, 1H ), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.16 (dd, 1H, J=17.5 Hz, J=2.0 Hz), 3.95 (dd, 1H, J=9.5 Hz, J=2.0 Hz), 3.75.about.3.10 (m, 6H)

IR (KBr, cm.sup.-1): 3330, 3300, 2950, 2850, 1700, 1610, 1250

Elemental analysis for C.sub.17 H.sub.18 O.sub.10 Calculated (%): C 53.40;H 4.75;O 41.85 Found (%): C 53.55;H 4.79;O 41.66

Compound 116

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.55 (m, 1H), 5.34 (m, 2H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.27 (t, 2H, J=6.2 Hz), 3.75.about.3.10 (m, 6H), 2.30.about.1.95 (m, 4H), 0.97 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 1700, 1640, 1605 1260

Elemental analysis for C.sub.21 H.sub.26 O.sub.10 Calculated (%):C 57.53;H 5.98;O 36.49 Found (%): C 57.75;H 5.79;O 36.46

Compound 117

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.10.about.7.00 (m, 2H), 5.40 (m, 1H), 5.37 (bs, 1H), 5.11 (m, 2H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 4.12 (d, 2H, J=8.5 Hz), 3.75.about.3.10 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s, 3H)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 1700, 1640, 1605, 1260

Elemental analysis for C.sub.25 H.sub.32 O.sub.10 Calculated (%): C 60.96;H 6.55;O 32.49 Found (%): C 60.85;H 6.75;O 32.40

Compound 118

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.19 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.35.about.7.20 (m, 5H), 7.10.about.7.00 (m, 2H), 5.37 (bs, 1H), 5.25 (s, 2H), 5.11 (bs, 1H), 5.05 (bs, 1H), 4.96 (d, 1H, J=6.8 Hz), 4.59 (bs, 1H), 3.75.about.3.10 (m, 6H)

IR (KBr, cm.sup.-1): 3330, 3300, 2950, 2850, 1700, 1620, 1260

Elemental analysis for C.sub.22 H.sub.22 O.sub.10 Calculated (%): C 59.19;H 4.97;O 35.84 Found (%): C 59.25;H 4.79;O 35.96

Compound 119

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.55 (s, 1H), 7.77 (d, 1H, J=8.8 Hz), 7.30.about.7.15 (m, 2H), 5.94 (s, 1H), 5.45.about.5.35 (m, 2H), 5.13 (t, 1H, J=10.0 Hz), 4.20.about.3.90 (m, 3H), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm.sup.-1): 3320, 2950, 1750, 1620, 1370, 1240

Elemental analysis for C.sub.25 H.sub.26 O.sub.15 Calculated (%): C 53.00;H 4.59;O 42.41 Found (%): C 52.95;H 4.55;O 42.50

Compound 120

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.30.about.7.15 (m, 2H), 5.94 (s, 1H), 5.45.about.5.35 (m, 2H), 5.13 (t, 1H, J=10 Hz),4.20.about.3.90 (m, 3H), 4.15 (s, 3H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.26 H.sub.28 O.sub.15 Calculated (%): C 53.79;H 4.83;O 41.38 Found (%): C 53.85;H 4.79;O 41.36

Compound 121

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.30.about.7.15 (m, 22H), 5.94 (s, 1H), 5.45.about.5.35 (m, 2H), 5.25 (m, 8H), 5.13 (t, 1H, J=10.0 Hz), 4.20.about.3.90 (m, 3H), 4.46 (t, 2H, J=6.0 Hz), 2.25 (q, 2H, J=7.2 Hz), 180.about.1.40 (m, 12H), 1.05 (t, 3H, J=7.2 Hz), 0.95 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2950, 2920, 2850, 1730, 1640, 1610, 1260

Elemental analysis for C.sub.54 H.sub.60 O.sub.11 Calculated (%): C 73.30;H 6.78;O 19.92 Found (%): C 73.35;H 6.80;O 19.85

Compound 122

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.35.about.7.20 (m, 20H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.94 (s, 1H), 5.45.about.5.35 (m, 2H), 5.30.about.5.18 (m, 8H), 5.13 (t, 1H, J=10.0 Hz), 4.20.about.3.90 (m, 3H), 4.46 (t, 2H, J=6.0 Hz), 2.23 (q, 2H, J=7.0 Hz), 1.95.about.1.40 (m, 16H), 1.07 (t, 3H, J=7.0Hz), 0.93 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2920, 2850, 1725, 1640, 1610, 1250

Elemental analysis for C.sub.56 H.sub.64 O.sub.11 Calculated (%):C 73.68;H 7.02;O19.30 Found (%):C 73.65;H 7.05;O 19.30

Compound 123

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.40.about.7.20 (m, 20H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.30.about.5.18 (m, 8H) 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.46 (t, 2H, J=6.0 Hz), 4.40.about.4.10 (m, 3H), 2.34 (s, 3H), 2.26 (q, 2H, J=7.0 Hz), 2.05.about.1.40 (m, 20H), 1.05 (t, 3H, J=7.0 Hz), 0.93 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2920, 2850, 1700, 1640, 1610, 1250

Elemental analysis for C.sub.58 H.sub.68 O.sub.11 Calculated (%): C 74.04;H 7.23;0 18.73 Found (%): C 74.08;H 7.35;O 18.57

Compound 124

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.40.about.7.20 (m, 20H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.18.about.5.30 (m, 8H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 4H), 2.25 (s, 3H), 1.05 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1610, 1250

Elemental analysis for C.sub.48 H.sub.48 O.sub.11 Calculated (%): C 72.00;H 6.00;O 22.00 Found (%): C 71.95;H 5.96;O 22.09

Compound 125

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.30.about.7.15 (m, 2H), 5.94 (s, 1H), 5.45.about.5.35 (m, 2H), 5.13 (t, 1H, J=10.0 Hz), 5.05 (m, 1H), 4.20.about.3.90 (m, 3H), 2.34 (s, 3H), 2.20.about.1.25 (m, 9H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 ((s, 3H), 0.95 (d, 3H, J=6.6 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.32 H.sub.38 O.sub.15 Calculated (%):C 58.00;H 5.74;O 36.26 Found (%):C 58.04;H 5.79;O 36.17

Compound 126

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.30.about.7.15 (m, 2H), 5.94 (s, 1H), 6.45 (dd, 1H, J=17.5 Hz, J=9.5 Hz); 5.45.about.5.35 (m, 2H), 5.13 (t, 1H, J=10.0 Hz), 4.20.about.3.90 (m, 5H), 2.34 (s, 3H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.27 H.sub.28 O.sub.15 Calculated (%): C 54.73;H 4.73;O 40.54 Found (%): C 54.75;H 4.79;O 40.46

Compound 127

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.34 (m, 2H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 5H), 2.34 (s, 3H), 2.30.about.1.95 (m, 4H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.97 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1610, 1250

Elemental analysis for C.sub.31 H.sub.360 O.sub.15 Calculated (%): C 57.41;H 5.56;O 37.03 Found (%): C 57.45;H 5.59;O 36.96

Compound 128

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz) 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.11 (m, 2H), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.22 (m, 3H), 4.12 (d, 2H, J=8.5 Hz), 2.30 (m, 4H), 2.05 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.67 (s, 6H), 1.60 (s, 3H), 1.55 (m,2H), 1.05 (t, 3H), J=6.9 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1620, 1260

Elemental analysis for C.sub.37 H.sub.46 O.sub.15 Calculated (%): C 60.82;H 6.30;O 32.88 Found (%): C 60.85;H 6.35;O 32.80

Compound 129

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.35.about.7.15 (m, 25H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.35.about.5.20 (m,10H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.15 (m, 3H), 2.25 (t, 2H, J=6.9 Hz), 1.56 (m, 2H), 1.04(t, 3H, J=6.9 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1705, 1620, 1260

Elemental analysis for C.sub.54 H.sub.52 O.sub.11 Calculated (%): C 73.97;H 5.94;O 20.09 Found (%): C 73.98;H 5.96;O 20.06

Compound 130

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.15 (s, 1H), 9.17 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.15 H.sub.16 O.sub.10 Calculated (%): C 50.56;H 4.53;O 44.91 Found (%): C 50.52;H 4.55;O 44.93

Compound 131

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.20 (s, 3H), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.16 H.sub.18 O.sub.10 Calculated (%): C 51.89;H 4.90;O 43.21 Found (%): C 51.83;H 4.85;O 43.32

Compound 132

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.20 (bs, 1H), 7.55 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.45 (t, 2H, J=6.4 Hz), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H), 180.about.1.30 (m, 12H), 0.87 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.23 H.sub.32 O.sub.10 Calculated (%): C 58.96;H 6.89;O 34.15 Found (%): C 58.95;H 6.85;O 34.20

Compound 133

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.42 (t, 2H, J=6.4 Hz), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H), 180.about.1.25 (m, 16H), 0.85 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.25 H.sub.36 O.sub.10 Calculated (%): C 60.47;H 7.31;O 32.22 Found (%): C 60.35;H 7.45;O 32.20

Compound 134

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.42 (t, 2H, J=6.4 Hz), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H), 1.90.about.1.25 (m, 20H), 0.85 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.27 H.sub.40 O.sub.10 Calculated (%): C 61.81;H 7.69;O 30.50 Found (%): C 61.75;H 7.45;O 30.80

Compound 135

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.28 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.45 (m, 1H), 3.85 (s, 1H), 3.75.about.3.10 (m, 6H), 1.05 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.18 H.sub.22 O.sub.10 Calculated (%): C 54.27;H 5.57;O 40.16 Found (%): C 54.10;H 5.65;O 40.25

Compound 136

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.99 (m, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 3.75.about.3.20 (m, 6H), 2.20.about.1.25 (m, 9H), 0.95 (d, 3H, J=6.7 Hz)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.22 H.sub.28 O.sub.10 Calculated (%):C 58.40;H 6.24;O 35.36 Found (%): C 58.43;H 6.35;O 35.22

Compound 137

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.17 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 6.45 (dd, 1H, J=17.5 Hz, J=9.5 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.15 (dd, 1H, J=17.5 Hz, J=2.0 Hz), 3.95 (dd, 1H, J=9.5 Hz, J=2.0 Hz), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.17 H.sub.18 O.sub.10 Calculated (%): C 53.40;H 4.75;O 41.85 Found (%): C 53.33;H 4.80;O 41.87

Compound 138

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.55 (m, 1H), 5.34 (m, 2H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.27 (t, 2H, J=6.2 Hz), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H), 2.30.about.1.95 (m, 4H), 0.97 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.21 H.sub.26 O.sub.10 Calculated (%): C 57.53;H 5.98;O 36.49 Found (%):C 57.57;H 5.85;O 36.58

Compound 139

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.41 (m, 1H), 5.13 (m, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 4.12 (d, 2H, J=8.5 Hz), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s, 3H)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.25 H.sub.32 O.sub.10 Calculated (%): C 60.96;H 6.55;O 32.49 Found (%): C 60.89;H 6.65;O 32.36

Compound 140

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.15 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.35 (m, 5H), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.23 (s, 2H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H)

IR (KBr, cm.sup.-1): 3335, 2950, 2920, 2850, 1690, 1630, 1610, 1250

Elemental analysis for C.sub.22 H.sub.22 O.sub.10 Calculated (%): C 59.19;H 4.97;O 35.84 Found (%): C 59.25;H 4.79;O 35.96

Compound 141

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.25 (bs, 1H), 7.77 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=2.4 Hz), 5.30.about.5.20 (m, 2H), 4.52(t, 1H, J=6.6 Hz), 4.11 (d, 2H, J=6.0 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H)

IR (KBr, cm.sup.-1): 2950, 1750, 1620, 1370, 1240

Elemental analysis for C.sub.25 H.sub.26 O.sub.15 Calculated (%): C 53.00;H 4.59;O 42.41 Found (%): C 52.95;H 4.55;O 42.50

Compound 142

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=2.4H 5.30.about.5.20 (m, 2H), 4.52 (t, 1H, J=6.6 Hz), 4.25 (s, 3H), 4.11 (d, 2H, J=6.0 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.26 H.sub.28 O.sub.15 Calculated (%): C 53.79;H 4.83;O 41.38 Found (%): C 53.85;H 4.79;O 41.36

Compound 143

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.35.about.7.20 (m, 20H), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=2.4 Hz), 5.30.about.5.20 (m, 2H), 5.30.about.5.18 (m, 8H), 4.52 (t, 1H, J=6.6 Hz), 4.46 (t, 2H, J=6.0 Hz), 4.11 (d, 2H, J=6.0 Hz), 1.95.about.1.40 (m, 16H), 2.30 (q, 2H, J=7.1 Hz), 1.10 (t, 3H, J=7.1 Hz), 0.93 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2920, 2850, 1725, 1640, 1610, 1250

Elemental analysis for C.sub.56 H.sub.64 O.sub.11 Calculated (%): C 73.68;H 7.02;O 19.30 Found (%):C 73.65;H 7.05;O 19.30

Compound 144

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.35.about.7.20 (m, 20H), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=2.4 Hz), 5.30.about.5.20 (m, 2H), 5.30.about.5.18 (m, 8H), 4.52 (t, 1H, J=6.6 Hz), 4.38 (t, 2H, J=6.0 Hz), 4.11 (d, 2H, J=6.0 Hz), 2.25 (q, 2H, J=7.2 Hz), 1.95.about.1.40 (m, 20H), 1.10 (t, 3H, J=7.2 Hz), 0.93 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2920, 2850, 1700, 1640, 1610, 1250

Elemental analysis for C.sub.58 H.sub.68 O.sub.11

Calculated (%): C 74.04;H 7.23;O 18.73 Found (%):C 74.08;H 7.35;O 18.57

Compound 145

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.40.about.7.20 (m, 20H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.30.about.5.18 (m, 8H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 4H), 2.25 (s, 3H), 1.05 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1610, 1250

Elemental analysis for C.sub.48 H.sub.48 O.sub.11 Calculated (%):C 72.00;H 6.00;O 22.00 Found (%): C 71.95;H 5.96;O 22.09

Compound 146

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=2.4 Hz), 5.30.about.5.20 (m, 2H), 5.02 (m, 1H), 4.52 (t, 1H, J=6.6 Hz), 4.11 (d, 2H, J=6.0 Hz), 2.34 (s, 3H), 2.25.about.1.24 (m, 9H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H), 0.97 (d, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.32 H.sub.38 O.sub.15 Calculated (%):C 58.00;H 5.74;O 36.26 Found (%):C 57.95;H 5.79;O 36.26

Compound 147

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 6.44 (dd, 1H, J=17.5 Hz, J=9.5 Hz), 5.66 (d, 1H, J=7.2 Hz), 5.38 (d, 1H, J=2.4 Hz), 5.30.about.5.20 (m, 2H), 4.52 (t, 1H, J=6.6 Hz), 4.20 (dd, 1H, J=17.5 Hz, J=2.0 Hz), 4.11 (d, 2H, J=6.0 Hz), 3.96 (dd, 1H, J=9.5 Hz, J=2.0 Hz), 2.34 (s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H), 1.96 (s, 3H)

IR (KBr, cm.sup.-1): 2950, 2850, 1725, 1610, 1250

Elemental analysis for C.sub.27 H.sub.28 O.sub.15 Calculated (%): C 54.73;H 4.73;O 40.54 Found (%): C 54.85;H 4.79;O 40.36

Compound 148

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.77 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz) 5.34 (m, 2H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.10 (m, 5H), 2.34 (s, 3H), 2.30.about.1.95 (m, 4H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 0.97 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1610, 1250

Elemental analysis for C.sub.31 H.sub.36 O.sub.15 Calculated (%):C 57.41;H 5.56;O 37.03 Found (%): C 57.45;H 5.59;O 36.96

Compound 149

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.11 (m, 2H), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.22 (m, 3H), 4.12 (d, 2H, J=8.5 Hz), 2.35 (m, 4H), 2.05 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H), 2.02 (s, 3H), 1.99 (s, 3H), 1.67 (s, 6H), 1.60 (s, 3H), 1.55 (m, 2H), 1.00 (t, 3H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1735, 1620, 1260

Elemental analysis for C.sub.37 H.sub.46 O.sub.15 Calculated (%): C 60.82;H 6.30;O 32.88 Found (%):C 60.85;H 6.35;O 32.80

Compound 150

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 7.65 (d, 1H, J=8.8 Hz), 7.35.about.7.15 (m, 25H), 7.12 (d, 1H, J=2.4 Hz), 7.06 (dd, 1H, J=2.4 Hz, J=8.8 Hz), 5.74 (d, 1H, J=7.6 Hz), 5.41 (t, 1H, J=9.4 Hz), 5.35.about.5.20 (m, 10H), 5.13 (dd, 1H, J=7.6 Hz, J=9.6 Hz), 5.04 (t, 1H, J=9.8 Hz), 4.40.about.4.15 (m, 3H), 2.25 (t, 2H, J=7.0 Hz), 1.55 (m, 2H), 1.00 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 2950, 2850, 1705, 1620, 1260

Elemental analysis for C.sub.54 H.sub.52 O.sub.11 Calculated (%):C 73.97;H 5.94;O 20.09 Found (%): C 73.94;H 5.96;O 20.10

Compound 151

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 10.24 (bs, 1H), 9.17 (bs, 1H), 7.61 (d, 1H, J=8.8 Hz), 7.12 (d, 1H, J=2.4 Hz), 7.07 (dd, 1H, J=2.2 Hz, J=9.0 Hz), 5.47 (s, 1H), 5.07 (bs, 1H), 4.85 (bs, 1H), 4.77 (bs, 1H), 3.85 (s, 1H), 3.75.about.3.20 (m, 6H)

IR (KBr, cm.sup.-1): 3400, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.15 H.sub.16 O.sub.10 Calculated (%): C 50.56;H 4.53;O 44.91 Found (%): C 50.52;H 4.55;O 44.93

Compound 152

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.35 (m, 5H), 7.10.about.7.00 (m, 2H), 5.28 (s, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs,1H), 3.65.about.3.25 (m, 6H)

IR (KBr, cm.sup.-1): 3330, 3300, 2950, 2850, 1700, 1620, 1260

Elemental analysis for C.sub.22 H.sub.22 O.sub.10 Calculated (%): C 59.19;H 4.97;O 35.84 Found (%): C 59.33;H 4.89;O 35.78

Compound 153

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), bs, 1H), 4.23 (s, 3H), 3.65.about.3.25 (m, 6H)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.16 H.sub.18 O.sub.10 Calculated (%): C 51.89;H 4.90;O 43.21 Found (%): C 51.85;H 4.78;O 43.37

Compound 154

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.47 (t, 2H, J=6.6 Hz), 3.65.about.3.25 (m, 6H), 1.80.about.1.70 (m, 2H), 1.60.about.1.20 (m, 14H), 0.90 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3400, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.25 H.sub.36 O.sub.10 Calculated (%):C 60.47;H 7.31;O 32.22 Found (%): C 60.45;H 7.40;O 32.15

Compound 155

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.10 (bs, 1H), 7.60 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.65 (bs, 1H), 4.52 (bs, 1H), 4.47 (t, 2H, J=6.6 Hz), 3.65.about.3.25 (m, 6H), 180.about.1.70 (m, 2H), 1.60.about.1.20 (m, 18H),0.90 (t, 3H, J=7.2 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.27 H.sub.40 O.sub.10 Calculated (%):C 61.81;H 7.69;O 30.50 Found (%):C 61.75;H 7.45;O 30.80

Compound 156

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.50 (m, 2H), 3.65.about.3.25 (m, 6H), 1.05 (d, 6H, J=7.5 Hz)

IR (KBr, cm.sup.-1): 3400, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.18 H.sub.22 O.sub.10 Calculated (%): C 54.27;H 5.57;O 40.16 Found (%): C 54.07;H 5.67;O 40.26

Compound 157

.sup.1 H-NMR (CDCl.sub.3, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.21 (bs, 1H), 5.00 (m, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 3.65.about.3.25 (m, 6H), 2.20.about.1.14 (m, 9H), 0.96 (d, 2H, J=6.8 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.22 H.sub.28 O.sub.10 Calculated (%):C 58.40;H 6.24;O 35.36 Found (%):C 58.25;H 6.38;O 35.37

Compound 158

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 6.45 (dd, 1H, J=17.5 Hz, J=9.5 Hz), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.15 (dd, 1H, J=17.5 Hz, J=2.0 Hz), 3.96 (dd, 1H, J=9.5 Hz, J=2.0 Hz), 3.65.about.3.25 (m, 6H)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 2850, 1680, 1630, 1610, 1250

Elemental analysis for C.sub.17 H.sub.18 O.sub.10 Calculated (%): C 53.40;H 4.75;O 41.85 Found (%): C 53.45;H 4.78;O 41.77

Compound 159

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.55 (m, 1H), 5.34 (m, 1H), 5.21 (bs, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.27 (t, 2H, J=6.2 Hz), 3.65.about.3.25 (m, 6H), 2.30.about.1.95 (m, 4H), 0.97 (t, 3H, J=7.0 Hz)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 1700, 1640, 1605, 1260

Elemental analysis for C.sub.21 H.sub.26 O.sub.10 Calculated (%):C 57.53;H 5.98;O 36.49 Found (%): C 57.77;H 5.85;O 36.38

Compound 160

.sup.1 H-NMR (DMSO-d.sub.6, .delta.-TMS): 9.16 (bs, 1H), 7.61 (d, 1H, J=9.6 Hz), 7.10.about.7.00 (m, 2H), 5.40 (m, 1H), 5.21 (bs, 1H), 5.11 (m, 1H), 4.92 (d, 1H, J=7.6 Hz), 4.88 (bs, 1H), 4.67 (bs, 1H), 4.52 (bs, 1H), 4.15 (d, 2H, J=8.5 Hz), 3.65.about.3.25 (m, 6H), 2.05 (m, 4H), 1.67 (s, 6H), 1.60 (s, 3H)

IR (KBr, cm.sup.-1): 3350, 2950, 2920, 1700, 1640, 1605, 1260

Elemental analysis for C.sub.25 H.sub.32 O.sub.10 Calculated (%):C 60.96;H 6.55;O 32.49 Found (%): C 60.83;H 6.62;O 32.55

TEST EXAMPLE 1

Acute toxicity test in mice

We performed this test in order to comfirm a degree of the safety on that the compounds of the present invention. In the following, the method of the acute toxicity test will be explained.

Method: 7-glycosyloxybenzopyran derivatives (compound No. 3, 8, 9, 11, 15, 16, 18.about.23, 35, 37.about.47, 61.about.72, 75, 86.about.96, 99, 108.about.118, 130.about.140, 145, 151.about.160) were forcibly administered orally at the doses of 1000 and 2000 mg/kg to Male ICR mice (body weight is 20.about.25 g, 5 mice per one(1) group), using an esophageal sound. After the administration, the animals were kept in cages for 7 days, to observed general symptoms and to count dead animals. Lethal dose (LD.sub.50 : mg/kg) was extrapolated from the mortality at 7th day after administration.

In result, the LD.sub.50 of all 7-glycosyloxybenzopyran derivatives were over 2000 mg/kg, and therefore it was clearly shown that the compounds of the present invention have extremely low toxicity.

TEST EXAMPLE 2

Effect on homologous passive cutaneous anaphylaxis (PCA) reaction in rats.

We performed this pharmacological test by PCA reaction which was well known screening test for anti-allergic agents in order to demonstrate that the compounds of the present invention possess anti-allergic activity. This experimental animal model is caused by immediate type allergic reaction namely, antigen-antibody reaction. In the following, the method of this pharmacological test will be explained.

Method: Male wistar rats (9 weeks old) were intradermally administered 0.05 ml of anti-serum against dinitrophenylated ascaris (DNP-As) into two sites on the shaved dorsal skin. 48 hours later, 7-glycosyloxybenzopyran derivatives (test compounds) suspended in 0.5% sodium carboxymethylcellulose (CMCNa) were given orally at a dose of 50 mg/kg to the animals. One hour after administration of Test compounds, the animals were induced anaphylaxis by injection of saline (1 ml) dissolving 5 mg of Evans Blue and 1 mg of Trinitrophenylated ascaris (TNP-As) into the tail vein of the animals. 30 minutes after induction of anaphylaxis, animals were anesthetized by ether and killed by bleeding, and were flayed dorsal skin. The determination of extravasated dye was performed according to the method of Katayama et al. (Microbiol. Immunol., Vol.22, P 89-101, 1978). As vehicle control group, only 0.5% CMCNa solution was administered orally, and as positive control group, Tranilast suspended in 0.5% CMCNa was administered orally at a dose of 100 mg/kg to the animals with the same method as the test compounds groups. Inhibition (%) of PCA reaction was calculated according to equation 1 and the result was shown in TABLE 2. Each experimental group consisted of 5 rats. ##EQU1##

In equation 1:

A: amount of dye in vehicle control group B: amount of dye in test compound group or in positive control group TABLE 2______________________________________compound No. Inhibition (%) compound No. Inhibition (%)______________________________________compound 3 53.1 compound 61 40.2compound 8 49.2 compound 62 53.2compound 9 54.5 compound 63 55.7compound 11 43.2 compound 64 54.9compound 15 40.1 compound 65 52.1compound 16 42.3 compound 66 49.3compound 18 42.5 compound 67 50.4compound 19 44.9 compound 68 49.5compound 20 42.3 compound 69 48.1compound 21 45.2 compound 70 51.3compound 22 43.6 compound 71 49.8compound 23 44.7 compound 72 45.2compound 35 42.2 compound 75 45.5compound 37 55.1 compound 86 56.4compound 38 59.3 compound 87 60.3compound 39 62.2 compound 88 61.5compound 40 57.3 compound 89 57.8compound 41 55.4 compound 90 54.3compound 42 56.4 compound 91 55.5compound 43 57.9 compound 92 58.9compound 44 54.5 compound 93 55.2compound 45 55.2 compound 94 53.7compound 46 54.3 compound 95 54.2compound 47 52.1 compound 96 50.1compound 99 40.2 compound 136 42.2compound 108 45.3 compound 137 41.7compound 109 42.1 compound 138 42.5compound 110 41.4 compound 139 41.8compound 111 43.1 compound 140 40.4compound 112 44.5 compound 145 40.2compound 113 40.3 compound 151 45.4compound 114 45.3 compound 152 41.3compound 115 42.2 compound 153 42.4compound 116 46.1 compound 154 43.2compound 117 40.3 compound 155 42.9compound 118 41.2 compound 156 42.1compound 130 40.1 compound 157 48.1compound 131 41.2 compound 158 44.3compound 132 42.9 compound 159 45.1compound 133 42.3 compound 160 43.9compound 134 41.5 Tranilast 54.6compound 135 40.3______________________________________

As shown in table 2, it was demonstrated that all compounds of the present invention have equivalent or superior anti-allergic activity to Tranilast. The results of these examples clearly showed that the compounds of the present invention were useful anti-allergic agent for immediate type allergic disease.

COMPARATIVE TEST EXAMPLE 1

Effect on homologous passive cutaneous anaphylaxis (PCA) reaction in rats

The anti-allergic activity of the compounds of the present invention were compared with that of analogous compounds which were published in the Patent (No. WO 92/13852) by PCA reaction. This pharmacological test was performed according to the method described in Test Example 2. The compared compounds were shown in table 3 and the results were shown in table 4.

TABLE 3______________________________________Comparedcompound No. Chemical name______________________________________Compared 4-hydroxy-3,7-dimethoxy-2H-1-benzopyran-2-onecompound 1Compared 3-butoxy-4-hydroxy-7-methoxy-2H-1-benzopyran-compound 2 2-oneCompared 3-hydroxy-4,7-dimethoxy-2H-1-benzopyran-2-onecompound 3Compared 3-hydroxy-4-butoxy-7-methoxy-2H-1-benzopyrancompound 4 2-one______________________________________ TABLE 4______________________________________ compound No.Compared com- of the presentpound No. Inhibition % invention Inhibition (%)______________________________________Compared compound 1 28.1 compound 3 53.1Compared compound 2 32.4 compound 9 54.5 compound 37 55.1 compound 86 56.4Compared compound 3 31.5 compound 109 42.1Compared compound 4 26.2 compound 153 42.4 compound 110 41.4 compound 18 42.5______________________________________

From the results of the Test Example 2 and this Comparative Test Example, it is clear that the anti-allergic activity of the compounds of the present invention, 7-glycoside, were higher than that of the compared compounds.

TEST EXAMPLE 3

Effect on contact dermatitis induced by picryl chloride in mice

We performed this pharmacological test by experimental contact dermatitis model which is well known in order to demonstrate that the compounds of the present invention suppress the delayed type hypersensitization. This experimental animal model which is typical delayed type hypersensitization model, was mainly caused by cellular immune response (Immunology, Vol. 15, P. 405-416, 1968). The delayed type hypersensitization is inhibited by steroid drugs,but can not be effected by known anti-allergic agents. In the following, the method of the pharmacological test will be explained.

Method: Mice, shaved their abdominal skin on previous day, were immunized by applying 0.1 ml of acetone containing 7 mg of picryl chloride to the skin of the abdomen. 7 days after immunization, the thickness of the ear was measured with a dial thickness gauge, then mice were challenged by painting 5 .mu.l of 1% picryl chloride olive oil solution to each side skin of left ear. 24 hours after challenge, the thickness of the left ear was measured again and the increase (%) of thickness was calculated according to equation 2. The compounds of the present invention (test compounds) suspended in 0.5% CMCNa were forcibly administered orally at a dose of 50 mg/kg at 1 hour before and 16 hours after challenge. As vehicle control group, only 0.5% CMCNa solution were administered orally, and as positive control group, Prednisolone, steroid hormone, and Tranilast were administered orally at the doses of 10 mg/kg and 100 mg/kg, respectively. The inhibition (%) against the increase of thickness in vehicle control group were calculated according to equation 2 and 3, the result was shown in TABLE 5.

Increase (%)=(A-B)/B.times.100 (Equation 2)

In equation 2:

A: thickness of the ear at 24 hours after challenge B: thickness of the ear before challenge Inhibition (%)=(C-D)/C.times.100 (equation 3)

In equation 3:

C: The increase (%) in vehicle control group D: The increase (%) in test compounds group or positive control group TABLE 5______________________________________compound No. Inhibition (%) compound No. Inhibition (%)______________________________________compound 3 51.3 compound 61 43.1compound 8 50.3 compound 62 49.3compound 9 52.1 compound 63 53.1compound 11 44.3 compound 64 52.6compound 15 41.2 compound 65 50.3compound 16 43.5 compound 66 51.4compound 18 40.2 compound 67 53.2compound 19 47.1 compound 68 47.3compound 20 45.2 compound 69 49.9compound 21 48.9 compound 70 52.1compound 22 47.3 compound 71 47.4compound 23 49.3 compound 72 42.3compound 35 40.5 compound 75 40.3compound 37 53.9 compound 86 59.4compound 38 63.7 compound 87 64.9compound 39 65.1 compound 88 66.8compound 40 62.1 compound 89 62.3compound 41 60.1 compound 90 60.1compound 42 58.3 compound 91 59.3compound 43 55.4 compound 92 57.2compound 44 56.3 compound 93 56.4compound 45 54.2 compound 94 51.2compound 46 57.6 compound 95 55.8compound 47 51.9 compound 96 48.9compound 99 40.3 compound 136 41.2compound 108 42.4 compound 137 43.5compound 109 43.8 compound 138 44.7compound 110 42.9 compound 139 42.1compound 111 41.2 compound 140 40.1compound 112 43.3 compound 145 42.1compound 113 45.5 compound 151 46.5compound 114 47.3 compound 152 43.2compound 115 40.2 compound 153 44.7compound 116 44.4 compound 154 41.6compound 117 42.3 compound 155 40.9compound 118 43.5 compound 156 43.2compound 130 41.2 compound 157 50.9compound 131 40.9 compound 158 48.2compound 132 43.2 compound 159 44.3compound 133 41.4 compound 160 46.7compound 134 43.7 Prednisolone 63.7compound 135 44.6 Tranilast 4.3______________________________________

It was observed that test compounds effectively inhibit the swelling of the ear by 40 to 65% against that in vehicle control group. Many of the compounds of the present invention were equivalent or superior to Prednisolone (inhition: 63.7%). In contrast, Tranilast, used widely for allergic disease, did not inhibit delayed type hypersensitization. These results clearly show that the compounds of the present invention have exceedingly inhibitory activity against delayed type hypersensitization. And therefore the compounds of the present invention is are exceedingly useful anti-allergic agent.

TEST EXAMPLE 4

Effect on experimental asthma model in guinea pigs

The asthma is typical allergic disease and we carried out this pharmacological test by well known experimental asthma model in guinea pigs in order to comfirm that the compounds of the present invention suppress the asthma. In the following, the method of the pharmacological test will be explained.

Method: Male hartley guinea pigs were immunized by intraperitoneal injection of saline (1ml) containing 5 mg of ovalbumine (OVA) three times at interval of one week. 2 weeks after final immunization, the animals were challenged by inhalation of 1% OVA-saline solution for 1 minute and then the airway resistance of the animals were measured for 30 minutes with PULMOS-1 (Medical Interface Project Station Inc.) after the inhalation. The compounds of the present invention (test compounds) suspended in 0.5% CMCNa were given orally at a dose of 50 mg/kg. As positive control group, Disodium Cromoglicate (DSCG), well known anti-allergic agent, in saline were injected at a dose of 20 mg/kg into the vein of the animals. As vehicle control group, only 0.5% CMCNa solution were given orally. The inhibition (%) of the airway resistance in vehicle control group was calculated according to equation 5 and the result was shown in TABLE 6. Each experimental group consisted of 5 guinea pigs. ##EQU2##

In equation 5:

A: Maximum airway resistance in vehicle control group B: Maximum airway resistance in test compounds group or positive control group TABLE 6______________________________________compound No. Inhibition (%) compound No. Inhibition (%)______________________________________compound 3 63.1 compound 61 45.2compound 8 59.2 compound 62 50.1compound 9 60.3 compound 63 53.2compound 11 45.7 compound 64 57.2compound 15 42.1 compound 65 49.3compound 16 40.2 compound 66 54.3compound 18 52.3 compound 67 60.2compound 19 65.2 compound 68 63.5compound 20 55.4 compound 69 59.3compound 21 63.1 compound 70 65.6compound 22 60.6 compound 71 63.2compound 23 61.5 compound 72 52.1compound 35 38.2 compound 75 43.5compound 37 68.2 compound 86 73.2compound 38 75.5 compound 87 79.5compound 39 77.8 compound 88 80.2compound 40 73.1 compound 89 77.3compound 41 70.2 compound 90 72.1compound 42 68.5 compound 91 69.5compound 43 70.7 compound 92 65.2compound 44 65.1 compound 93 69.7compound 45 62.3 compound 94 73.2compound 46 63.4 compound 95 63.2compound 47 59.1 compound 96 58.2compound 99 39.2 compound 136 51.2compound 108 50.1 compound 137 45.4compound 109 53.1 compound 138 50.8compound 110 56.5 compound 139 47.2compound 111 61.3 compound 140 45.1compound 112 57.2 compound 145 41.9compound 113 56.6 compound 151 49.7compound 114 59.7 compound 152 52.4compound 115 53.1 compound 153 54.3compound 116 62.8 compound 154 59.2compound 117 49.4 compound 155 57.6compound 118 45.3 compound 156 48.2compound 130 40.2 compound 157 55.7compound 131 42.5 compound 158 42.3compound 132 50.1 compound 159 52.3compound 133 43.2 compound 160 58.9compound 134 45.9 DSCG 51.2compound 135 47.1______________________________________

As shown in Table 6, the compounds of the present invention administered orally inhibited the increase of the airway resistance by 40.about.80%. Therefore the compounds of the present invention have exceedingly high activity to treat for the asthma.

______________________________________FORMULATION EXAMPLE 1(5% powders)______________________________________ compound 43 50 mg lactose 950 mg 1000 mg______________________________________

Crystals of the compound 43 were pulverized in a mortar and thoroughly mixed with by pulverizing the mixture with a pestle to obtain 5% powders.

______________________________________FORMULATION EXAMPLE 2(5% powders)______________________________________compound 154 50 mglactose 950 mg 1000 mg______________________________________

The procedure of Formulation Example 1 was repeated to obtain 5% powders.

______________________________________FORMULATION EXAMPLE 3(10% granules)______________________________________ compound 62 300 mg lactose 2000 mg starch 670 mg gelatin 30 mg 3000 mg______________________________________

The compound 62 was mixed with the same amount of starch and pulverized in a mortar. This was further mixed with lactose and the remaining portion of starch. Separately from this, 30 mg of gelatin was mixed with 1 ml of purified water, solubilized by heating, cooled and then, with stirring, mixed with 1 ml of ethanol to prepare a gelatin solution. Thereafter, the mixture prepared above was mixed with the gelatin solution, and the resulting mixture was kneaded, granulated and then dried to obtain granules.

______________________________________FORMULATION EXAMPLE 4(10% granules)______________________________________compound 132 300 mglactose 2000 mgstarch 670 mggelatin 30 mg 3000 mg______________________________________

The procedure of Formulation Example 3 was repeated to obtain 10% granules.

______________________________________FORMULATION EXAMPLE 5(5 mg tablets)______________________________________compound 21 5 mglactose 62 mgstarch 30 mgtalc 2 mgmagnesium stearate 1 mg 100 mg/tablet______________________________________

A 20 times larger portion of the above composition was used to prepare tablets each of which containing 5 mg of the compound 21. That is, 100 mg of the compound 21 in a crystal form was pulverized in a mortar and mixed with lactose and starch. The thus prepared formulation was mixed with 10% starch paste, and the mixture was kneaded and then subjected to granulation. After drying, the resulting granules were mixed with talc and magnesium stearate and subjected to tablet making in the usual way.

______________________________________FORMULATION EXAMPLE 6(5 mg tablets)______________________________________compound 110 5 mglactose 62 mgstarch 30 mgtalc 2 mgmagnesium stearate 1 mg 100 mg/tablet______________________________________

The procedure of Formulation Example 5 was repeated to obtain 5 mg tablets.

______________________________________FORMULATION EXAMPLE 7(20 mg tablets)______________________________________compound 22 20 mg6% hydroxypropylcellulose/lactose 75 mgstearate/talc 2 mgpotato starch 3 mg 100 mg/tablet______________________________________

A 10 times larger portion of the above composition was used to prepare tablets each of which containing 20 mg of the active ingredient. That is, 6 g of hydroxypropylcellulose was dissolved in an appropriate volume of ethanol and mixed with 94 g of lactose, followed by kneading. After drying to a degree, the mixture was passed through a No.60 mesh, and the thus graded granules were used as 6% hydroxypropylcellulose/lactose. Separately from this, magnesium stearate and talc were mixed at a ratio 1:4 and used as stearate/talc. Thereafter, the compound 22, 6% hydroxypropylcellulose/lactose, stearate/talc and potato starch were thoroughly mixed and subjected to tablet making in the usual way.

______________________________________FORMULATION EXAMPLE 8(20 mg tablets)______________________________________compound 87 20 mg6% hydroxypropylcellulose/lactose 75 mgstearate/talc 2 mgpotato starch 3 mg 100 mg/tablet______________________________________

The procedure of Formulation Example 7 was repeated to obtain 20 mg tablets.

______________________________________FORMULATION EXAMPLE 9(25 mg tablets)______________________________________compound 68 25 mglactose 122 mgcarboxyethylstarch 50 mgtalc 2 mgmagnesium stearate 1 mg 200 mg/tablet______________________________________

Ten times larger portions of the above compounds were put into a mortar to prepare tablets each of which containing 25 mg of the active ingredient. That is, 250 mg of the compound 68 in a crystal form was pulverized in a mortar and thoroughly mixed with lactose. An appropriate volume of purified water was added to carboxyethylstarch which was subsequently added to the above mixture, and the resulting mixture was kneaded and then subjected to granulation. After drying, the thus prepared granules were mixed with talc and magnesium stearate and subjected to tablet making in the usual way.

______________________________________FORMULATION EXAMPLE 10(25 mg tablets)______________________________________compound 153 25 mglactose 122 mgcarboxyethylstarch 50 mgtalc 2 mgmagnesium stearate 1 mg 200 mg/tablet______________________________________

The procedure of Formulation Example 9 was repeated to obtain 25 mg tablets.

______________________________________FORMULATION EXAMPLE 11(10 mg capsules)______________________________________compound 38 300 mglactose 2000 mgstarch 670 mggelatin 30 mg 3000 mg______________________________________

Granules were prepared in accordance with the procedure described in Formulation Example 3 and packed in capsules in 100 mg portions.

______________________________________FORMULATION EXAMPLE 12(10 mg capsules)______________________________________compound 116 300 mglactose 2000 mgstarch 670 mggelatin 30 mg 3000 mg______________________________________

The procedure of Formulation Example 11 was repeated to obtain 100 mg capsules.

______________________________________FORMULATION EXAMPLE 13(0.1% injections)______________________________________compound 3 10 mgpolyethylene glycol 400 3 mlpolysorbate 80 0.01 mldistilled water for injection use balance 10 ml______________________________________

The compound 3 was dissolved in a mixture solution of polyethylene glycol 400 and polysorbate 80, total volume of the resulting solution was adjusted to 10 ml by gradually adding distilled water for injection use and then the thus prepared solution was packed in an ampule aseptically.

______________________________________FORMULATION EXAMPLE 14(0.1% injections)______________________________________compound 18 10 mgpolyethylene glycol 400 3 mlpolysorbate 80 0.01 mldistilled water for injection use balance 10 ml______________________________________

The procedure of Formulation Example 13 was repeated to obtain 0.1% injections.

Thus, it is apparent that there has been provided, in accordance with the present invention, a novel 7-glycosyloxybenzopyran derivative which is useful in pharmaceutical preparations. Also provided are excellent antiallergic agents which have low toxicity and are useful for the treatment or prevention of immediate type and delayed type allergic diseases, particularly an excellent antiallergic agent which is highly effective on delayed type allergy that cannot be treated effectively with the prior art antiallergic agents.

While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.

Claims

1. A 7-glycosyloxybenzopyran derivative represented by the following formula (I) ##STR5## wherein, R.sub.1 is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group, R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group and R.sub.3 is a glycosyl group whose hydroxyl group is protected or not protected, selected from the group consisting of glucosyl, mannosyl and galactosyl groups; or physiologically acceptable salts thereof.

2. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as claimed in claim 1 wherein R.sub.1 is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group and R.sub.2 is a hydrogen atom or an aralkyl group.

3. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as claimed in claim 1 wherein R.sub.1 is a hydrogen atom or an acyl group and R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group.

4. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as claimed in claim 1 wherein R.sub.1 is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group and R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group.

5. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein the acyl group is an alkanoyl group and the aralkyl group is a benzyl group.

6. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.1 is an alkyl group having 1 to 12 carbon atoms.

7. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.1 is a cycloalkyl group having 5 to 8 carbon atoms.

8. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.1 is an alkenyl group having 2 to 10 carbon atoms.

9. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as claimed in claim 4 wherein R.sub.1 is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms or an alkenyl group having 2 to 10 carbon atoms and R.sub.2 is a hydrogen atom.

10. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.2 is an alkyl group having 1 to 12 carbon atoms.

11. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.2 is a cycloalkyl group having 5 to 8 carbon atoms.

12. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.2 is an alkenyl group having 2 to 10 carbon atoms.

13. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as claimed in claim 4 wherein R.sub.1 is a hydrogen atom and R.sub.2 is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.

14. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.3 is a glucosyl group.

15. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.3 is a mannosyl group.

16. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.3 is a galactosyl group.

17. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.3 is an unprotected glucosyl group.

18. The 7-glycosyloxybenzopyran derivative and physiologically acceptable salts thereof as in claim 1 wherein R.sub.3 is a glucosyl group which is protected with an acyl or aralkyl group.

19. An antiallergic composition comprising a therapeutically effective amount of the compound of formula (I) as recited in claim 1, or a pysiologically acceptable salt thereof, and pharmaceutically acceptable carriers.

20. The antiallergic composition as claimed in claim 19 wherein R.sub.1 is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group and R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group or an alkenyl group.

21. The antiallergic composition as claimed in claim 20 wherein R.sub.1 is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.

22. The antiallergic composition as claimed in claim 20 wherein R.sub.1 is a hydrogen atom and R.sub.2 is an alkyl group, a cycloalkyl group or an alkenyl group.

23. The antiallergic composition as claimed in claim 20 wherein R.sub.1 is an alkyl group, a cycloalkyl group or an alkenyl group and R.sub.2 is a hydrogen atom.

24. The antiallergic composition as claimed in claim 23 wherein R.sub.1 is an alkyl group having 1 to 12 carbon atoms.

25. The antiallergic composition as claimed in claim 23 wherein R.sub.1 is a cycloalkyl group having 5 to 8 carbon atoms.

26. The antiallergic composition as claimed in claim 23 wherein R.sub.1 is an alkenyl group having 2 to 10 carbon atoms.

27. The antiallergic composition as in claim 19 wherein R.sub.3 is a glucosyl group.

28. The antiallergic composition as in claim 19 wherein R.sub.3 is a mannosyl group.

29. The antiallergic composition as in claim 19 wherein R.sub.3 is a galactosyl group.

30. The antiallergic composition as in claim 19 wherein R.sub.3 is an unprotected glucosyl group.

31. The antiallergic composition as in claim 19 wherein R.sub.3 is a glucosyl group which is protected with an acyl or aralkyl group.

32. A pharmaceutical composition comprising the compound of formula (I) as recited in claim 1 and nontoxic additives.

33. A method for treating allergic diseases which comprises administering to a mammal in need of such treatment a therapeutically effective amount of the compound of formula (I) as recited in claim 1 or a pysiologically acceptable salt thereof.