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Synthesis and antiviral evaluation of enantiomeric 2′,3′-dideoxy- and 2′,3′-didehydro-2′,3′-dideoxy-4′-thionucleosides

✍ Scribed by Robert J. Young; Sue Shaw-Ponter; Jamie B. Thomson; J.Allen Miller; John G. Cumming; Ashley W. Pugh; Peter Rider

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 325 KB
Volume: 5
Category: Article
ISSN: 0960-894X
DOI: 10.1016/0960-894x(95)00472-6

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✦ Synopsis

The synthesis and antiviral evaluation of 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy 4'thionucleosides in both enantiomeric series are described. Enantiomeric 4-O-silylated-4hydroxymethyl-4-thiobutyrolactones, produced in high yield from chiral glycidols, provided suitable chiral synthons: phenylselenation of these intermediates resulted in anomeric selectivity in nucleobase glycosidations. L-d4-cytidine analogues showed marked anti-HBV and anti-HIV activity.

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