Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV

Abstract

A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromo-benzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give a requisite methyl furanoside derivative which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the α- and β-nucleoside analogues