An alternative strategy for the synthesis of 3′-azido-2′,3′-dideoxy-4′-thionucleosides starting from d-xylose

Methyl 5-O- acetyl-3-azido-2,3-dideoxy-4-thio-α,β- d-erythro- pentofuranoside and 1,5-O- diacetyl-3-azido-2,3-dideoxy-4-thio-α,β- d-erythro- pentofuranose were prepared in twelve and thirteen steps, respectively, by an efficient route starting from d-xylose. Both compounds were easily converted into...

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Bibliographic Details
Published in:Carbohydrate research 1995-02, Vol.267 (2), p.203-215
Main Authors: Tber, Bougrine, Fahmi, Nour-Eddine, Ronco, Gino, Villa, Pierre, Ewing, David F., Mackenzie, Grahame
Format: Article
Language:English
Subjects:
4,5-Epithiopentose
4′-Thiouridine nucleosides
Double inversion
ThioAZT
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Summary:Methyl 5-O- acetyl-3-azido-2,3-dideoxy-4-thio-α,β- d-erythro- pentofuranoside and 1,5-O- diacetyl-3-azido-2,3-dideoxy-4-thio-α,β- d-erythro- pentofuranose were prepared in twelve and thirteen steps, respectively, by an efficient route starting from d-xylose. Both compounds were easily converted into an anomeric mixture of pyrimidine nucleosides by reaction with the 2,4-bi(trimethylsilyloxy) derivative in the presence of a Lewis acid. The anomeric mixtures were separated by chromatography. The 4′-thio analogue of AZT and related uridine nucleosides have been prepared by a novel and more efficient approach.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(94)00296-R