An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly

An economical synthesis of lamivudine was developed by employing a new method to establish the stereochemistry about the heterocyclic oxathiolane ring. Toward this end, an inexpensive and readily accessible lactic acid derivative served the dual purpose of activating the carbohydrate’s anomeric cent...

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Bibliographic Details
Published in:Organic process research & development 2020-06, Vol.24 (6), p.1194-1198
Main Authors: Snead, David R., McQuade, D. Tyler, Ahmad, Saeed, Krack, Rudy, Stringham, Rodger W., Burns, Justina M., Abdiaj, Irini, Gopalsamuthiram, Vijayagopal, Nelson, Ryan C., Gupton, B. Frank
Format: Article
Language:English
Subjects:
Communication
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Summary:An economical synthesis of lamivudine was developed by employing a new method to establish the stereochemistry about the heterocyclic oxathiolane ring. Toward this end, an inexpensive and readily accessible lactic acid derivative served the dual purpose of activating the carbohydrate’s anomeric center for N-glycosylation and transferring stereochemical information to the substrate simultaneously. Both enantiomers of the lactic acid derivative are available, and either β-enantiomer in this challenging class of 2′-deoxynucleoside active pharmaceutical ingredients can be formed.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.0c00083