One vessel stereoselective glycosylation of purines and pyrimidines
US5602245A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Nov 4, 1992 |
| Grant date | Feb 11, 1997 |
| Priority date | — |
| Expiry date | Nov 4, 2012 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H19/16
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process for the preparation of 2',3' dideoxynucleosides, 2'-deoxynucleosides, and 2',3'-dideoxy-2',3'-didehydronucleosides is provided that includes the synchronous addition of a stereoselecting moiety (a directing group) and a protected purine or pyrimidine base to 5-(S)-6-(protected-oxy)-4,5-dihydrofuran in the presence of a Lewis acid. This one vessel reaction eliminates the need to separately prepare and purify a 2'-substituted ribose derivative that in a second step is condensed with a purine or pyrimidine base. The process can be easily modified to increase the stereoselectivity of formation of the .beta.-anomeric nucleoside as necessary.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.