Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
US4195174A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Apr 7, 1978 |
| Grant date | Mar 25, 1980 |
| Priority date | — |
| Expiry date | Apr 7, 1998 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H15/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.