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Synthesis of 3′-azido-2′,3′-dideoxy-β-D-arabino-hexopyranosyl nucleosides

✍ Scribed by Hansen, Poul ;Lau, Jesper ;Pedersen, Erik B. ;Nielsen, Carsten M.

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 439 KB
Volume: 1990
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1990199001194

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✦ Synopsis

Abstract

The α,β‐unsaturated D‐sugar aldehyde 2, prepared from tri‐O‐acetyl‐D‐glucal, was converted into 1‐O‐acetyl‐3‐azido‐2,3‐dideoxy‐α‐D‐arabino‐pyranose (3) by reaction with sodium azide in a mixture of acetic acid and water followed by acetylation. Reaction of 3 with silylated pyrimidines using TMS triflate as catalyst followed by deprotection with saturated ammonia in methanol afforded 3′‐azido‐2′,3′‐dideoxy‐β‐D‐arabino‐hexopyranosyl nucleosides 4.

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