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

Article abstract of DOI:10.1016/0008-6215(94)00296-R

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.