Claims
- 1. A method for making a compound having the structure: ##STR50## comprising the following steps (a) adding 6-deoxy-.alpha.-L-mannopyranosyl bromide, 2,3,4-tri-O-benzoate; DMSO; a base, selected from the group including tertiary amines, amidines, bicarbonates, carbonates, heteroaryl amine, and a solvent, hydrocarbons, esters, and ethers, in a slurry heated to 50.degree.-150.degree. C.;
- (b) stirring the reaction mixture at 50.degree.-150.degree. C. for 5 minutes to 30 minutes;
- (c) pouring the reaction mixture over ice water; and
- (d) extracting the product with a solvent selected from the group consisting of chlorinated solvents, aromatic hydrocarbons, esters, ethers, and evaporating said layer to give a solid.
- 2. A compound according to claim 1 wherein the solvent in step (a) is deleted and quantities of DMSO are increased so that DMSO is used both as a reactant and a solvent.
- 3. A compound according to claim 1 wherein the solvent of step (a) is dimethoxyethane.
- 4. A compound according to claim 1 wherein the temperature of the reaction mixture in steps (a) and (b) is 60.degree.-90.degree. C.
- 5. A compound according to claim 4 wherein the temperature is approximately 70.degree. C.
- 6. A compound according to claim 1 wherein the solvent of step (d) is EtOAc.
- 7. A compound according to claim 1 wherein the base of step (a) is triethylamine.
- 8. A compound according to claim 1 wherein:
- 1) step (a) is conducted with 6-deoxy-.alpha.-L-mannopyranosyl bromide, 2,3,4-tri-O-benzoate and DMSO and wherein DMSO is used in quantities so that it may be used as both a reactant and a solvent;
- 2) the reaction mixture in steps (a) and (b) is heated and stirred at approximately 70.degree. C.;
- 3) the extraction in step (d) is performed with EtOAc; and
- 4) the base solution used in step (a) is triethylamine.
Parent Case Info
This is a division of application Ser. No. 08/299,456, filed on Sep. 6, 1994, now abandoned, which is a continuation-in-part of Ser. No. 08/126,456 filed on Sep. 24, 1993 (now abandoned)
Non-Patent Literature Citations (4)
Entry |
Varela et al., Carbohydrate Chemistry, vol. 79: 219-224, (1980). |
Russell et al., Carbohydrate Research, vol. 201: 95-114, (1990). |
Nin et al., Synthesis, pp. 73-74, (Jan. 1991). |
Lichtenthaler et al., Liebigs Ann. Chem., pp. 1153-1161, (1989). |
Divisions (1)
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Number |
Date |
Country |
Parent |
299456 |
Sep 1994 |
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Continuation in Parts (1)
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Number |
Date |
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126456 |
Sep 1993 |
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