Synthesis of mannojirimycin derivatives
US5011929A · kind A · utility
8Cited by
1References
6Claims
0Family size
Assignee
Inventors
Key dates
| Filing date | Oct 11, 1989 |
| Grant date | Apr 30, 1991 |
| Priority date | — |
| Expiry date | Oct 11, 2009 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
.alpha.-Homojirimycin and 6-dpi-homojirimycin are each synthesized from 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-l actone in which the side chain acetonide is hydrolyzed to give the corresponding diol which is then protected with a silyl protecting agent to form a silyl ether. The latter compound is used as a divergent intermediate in which the piperidine ring is formed by joining the nitrogen function at C-2 to C-6 (A) with inversion of configuration at C-6 to form 6-epi-homomannojirimycin or (B) with retention of configuration at C-6 to form .alpha.-homomannojirimycin.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.