One vessel stereoselective glycosylation of purines and pyrimidi

Details One vessel stereoselective glycosylation of purines and pyrimidi One vessel stereoselective glycosylation of purines and pyrimidi

1992-11-04

1997-02-11

Kunz, Gary L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

549479, 568 65, C07H 100, C07H 1900, C07C31314, C07D30510

Patent

active

056022450

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.

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