Synthesis and Anti-HIV Activity of a New Hexopyranoside Analogue of AZT

Abstract
The glycosylation of thymine (13) with 12 in the presence of trimethylsilyl triflate promoter afforded the α, β-L-ribo-hexopyranosy1-nucleoside analogue 14a,b. After removal of the protecting group 1-(3-azido-2,3,6-trideoxy-α and β-L-ribo-hexopyranosyl) -thymine (15a and 15b) were isolated in anomerically pure form in a ratio of 1:20. The anti-HIV activity of the major product 15b was examined, in comparison with AZT, on H9 lymphoid cell-line.

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