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Synthesis of Potentially Antiviral 2′,3′-Dideoxy-2′-fluoro-3′-(hydroxyamino)nucleosides

✍ Scribed by Songqing Wang; Junbiao Chang; Shifeng Pan; Kang Zhao

Publisher: John Wiley and Sons
Year: 2004
Tongue: German
Weight: 205 KB
Volume: 87
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200490030

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✦ Synopsis

Abstract

A series of novel 3′‐(alkyl(hydroxy)amino)‐2′‐fluoronucleoside analogs were prepared via conjugate addition of N‐methylhydroxylamine to various 2‐fluorobutenolides. The adducts 13a and 16 were obtained as single isomers under absolute control of stereochemistry. The crucial N‐demethylation of 23–25 was readily achieved by means of DDQ oxidation, followed by nitrone/oxime exchange reaction. By this procedure, a variety of alkyl groups could be efficiently introduced at the 3′‐N‐atom of the nucleoside analogs, some of which might display potentially interesting anti‐HIV properties.

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