Azidochlorination and diazidization of glycals
US4935503A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | May 5, 1988 |
| Grant date | Jun 19, 1990 |
| Priority date | — |
| Expiry date | May 5, 2008 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H15/18
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The invention describes a one-pot single step procedure for the azidochlorination or diazidization of glycals, including glycal elements of carbohydrates. Compounds such as 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-D-galactopyranosy chloride, and 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-,beta-D-galactopyranose are prepared from tri-O-benzyl galactal as well as 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-alpha-galactopyranasol chloride and 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azi do-2-deoxy-alpha-D-glycopyranosyl chloride from their respective O-acetylated glycal derivatives by the addition of azido chloride which is chemically generated in situ. A method using 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride for the synthesis of antigenic determinants such as the terminal asialo GM.sub.1 (beta-D-Gal (1->3)-beta-D-GalNAc-OR) has been demonstrated. The conversion of the subject synthon into 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide and 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose is also described. A further method for the synthetic generation of the Tn antigen (alpha-D-GalNAc-O-L-serine) is als…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.