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Synthesis of 3′‐azido‐2′,3′‐dideoxy‐β‐ D ‐ arabino ‐hexopyranosyl nucleosides
Author(s) -
Hansen Poul,
Lau Jesper,
Pedersen Erik B.,
Nielsen Carsten M.
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001194
Subject(s) - chemistry , sodium azide , methanol , aldehyde , pyranose , trifluoromethanesulfonate , acetic acid , sugar , azide , organic chemistry , ammonia , medicinal chemistry , catalysis
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 .