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

ABSTRACT: 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 ?-enantiomer in this challenging class of 2'-deoxynucleoside active pharmaceutical ingredients can be formed.

SUBMITTER: Snead DR

PROVIDER: S-EPMC7309434 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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

Snead David R DR McQuade D Tyler DT Ahmad Saeed S Krack Rudy R Stringham Rodger W RW Burns Justina M JM Abdiaj Irini I Gopalsamuthiram Vijayagopal V Nelson Ryan C RC Gupton B Frank BF

Organic process research & development 20200407 6

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 challe ...[more]

PMID: 32587454

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