Claims
- 1. A process which comprises:
- reacting 3,4,6-tri-O-acetyl-D-galactal with ceric ammonium nitrate and an azide salt in a suitable solvent with stirring to form 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrates;
- reacting the 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrates with an iodide salt in a suitable solvent to obtain 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.alpha.-D-galactopyranosyl iodide;
- reacting 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.alpha.-D-galactopyranosyl iodide with a chloride salt in a suitable solvent to produce 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.beta.-D-galactopyranosyl chloride; and
- reacting 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.beta.-D-galactopyranosyl chloride with an alcohol selected from the group consisting of lower aliphatic alcohols, ROH, where R=(CH.sub.2).sub.n CO.sub.2 R', n=3-19 and R' is a lower alkyl or monocyclic aryl group, a monosaccharide having the structure ##STR5## where n=3-19 and R' is a lower alkyl or monocyclic aryl group, and a disaccharide having the structure ##STR6## where n=3-19 and R' is a lower alkyl or monocyclic aryl group, in the presence of a promoter to produce a 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.alpha.-D-galactopyranoside.
- 2. The process of claim 1 wherein the disaccharide is 8-methoxycarbonyloctyl-2-O-(2,3,4-tri-O-benzyl-.alpha.-L-fucopyranosyl)-4,6-O-benzylidene-.beta.-D-galactopyranoside.
- 3. A process which comprises:
- reacting 3,4,6-tri-O-acetyl-D-galactal with ceric ammonium nitrate and an azide salt in a suitable solvent with stirring to form 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrates;
- reacting the 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrates with a halide salt in a suitable solvent to form 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.alpha.-D-galactopyranosyl halide; and
- reacting the 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.alpha.-D-galactopyranosyl halide with an alcohol selected from the group consisting of lower aliphatic alcohols and ROH, where R=(CH.sub.2).sub.n CO.sub.2 R', n=3-19 and R' is a lower alkyl or monocyclic aryl group, in the presence of a promoter to produce 3,4,6-tri-O-acetyl-2-azido-2-deoxy-.beta.-D-galactopyranoside.
- 4. A process which comprises:
- reacting hexa-O-acyl-D-lactal with an azide salt in a suitable solvent with stirring to form 3,6-di-O-acyl-4-O-(2,3,4,6-tetra-O-acyl-.beta.-D-galactopyranosyl)-2-azido-2-deoxy-D-glucopyranosyl nitrate;
- reacting the acylated 2-azido-2-deoxy glycosyl nitrate with a halide salt in a suitable solvent to form 3,6-di-O-acyl-4-O-(2,3,4,6-tetra-O-acyl-.beta.-D-galactopyranosyl)-2-azido-2-deoxy-.alpha.-D-glucopyranosyl halide;
- reacting the peracylated 2-azido-2-deoxy-.alpha.-D-lactosyl halide with an alcohol selected from the group consisting of lower aliphatic alcohols and ROH, where R=(CH.sub.2).sub.n CO.sub.2 R', n=3-19 and R' is a lower alkyl or monocyclic aryl group, in the presence of a promoter to produce peracylated 2-azido-2-deoxy-.beta.-D-lactosides.
- 5. The process of claim 2 which includes deblocking the trisaccharide, reducing the azido group to give an amine and acetylating the amine to give 8-methoxycarbonyloctyl 3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-2-O-(.alpha.-L-fucopyranosyl)-.beta.-D-galactopyranoside.
- 6. The product having the structure ##STR7## where n=3-19 and R' is a lower alkoxy, monocyclic aryloxy, OH, NHNH.sub.2, or N.sub.3 group.
- 7. 8-Methoxycarbonyloctyl 3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-2-O-(.alpha.-L-fucopyranosyl)-.beta.-D-galactopyranoside.
- 8. The process of claim 5 which includes attaching the product of claim 5 through an amide linkage of the carbonyl group of the --(CH.sub.2).sub.n CO.sub.2 R' bridging arm to an insoluble aminated solid immunoabsorbent-type support, to form an immunoabsorbent.
- 9. The process of claim 5 which includes attaching the product of claim 5, through an amide linkage of the carbonyl group of the --(CH.sub.2).sub.n CO.sub.2 R' bridging arm to a soluble aminated or amine-containing antigen-forming carrier molecule, to form an antigen.
- 10. The process which comprises attaching 8-methoxycarbonyloctyl-3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-2-O-(.alpha.-L-fucopyranosyl)-.beta.-D-galactopyranoside through an amide linkage of the carbonyl group of the 8-methoxycarbonyloctyl bridging arm to an insoluble aminated solid immunoabsorbent-type support to form an immunoabsorbent.
- 11. The immunoabsorbent comprising 8-methoxycarbonyloctyl-3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-2-O-(.alpha.-L-fucopyranosyl)-.beta.-D-galactopyranoside attached, through an amide linkage of the carbonyl group of the 8-methoxycarbonyloctyl bridging arm, to an insoluble aminated solid immunoabsorbent-type support.
- 12. The product having the structure ##STR8## wherein n=3-19 and R' is a lower alkoxy, monocyclic aryloxy, OH, NHNH.sub.2, or N.sub.3 group.
- 13. 8-Methoxycarbonyloctyl 3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-.beta.-D-galactopyranoside.
- 14. The immunoabsorbent comprising 8-methoxycarbonyloctyl-3-O-(2-acetamido-2-deoxy-.alpha.-D-galactopyranosyl)-.beta.-D-galactopyranoside attached, through an amide linkage of the carbonyl group of the 8-methoxycarbonyloctyl bridging arm, to an insoluble aminated solid immunoabsorbent-type support.
- 15. The process of claim 1 wherein the monosaccharide is 8-methoxycarbonyloctyl-4,6-O-benzylidene-2-O-benzoyl-.beta.-D-galactopyranoside.
Parent Case Info
This is a division of application Ser. No. 894,366 filed Apr. 7, 1978, now U.S. Pat. No. 4,195,174.
US Referenced Citations (9)
Non-Patent Literature Citations (2)
Entry |
Paulsen et al., "Chem. Ber.", vol. 112, 1979, pp. 3190-3202. |
Paulsen et al., "Carbohydrate Research", vol. 64, pp. 339-364, 1978. |
Divisions (1)
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Number |
Date |
Country |
Parent |
894366 |
Apr 1978 |
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