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

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...

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Bibliographic Details
Published in:Helvetica chimica acta 2004-02, Vol.87 (2), p.327-339
Main Authors: Wang, Songqing, Chang, Junbiao, Pan, Shifeng, Zhao, Kang
Format: Article
Language:English
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Summary: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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200490030