Synthesis of 1-(3′-Azido-2′,3′-dideoxy-α-L-threo-pentofuranosyl)thymine as a Potential Anti-HIV Agent

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Abstract
Starting from methyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside, a multistep synthesis of the C-4′ epimer of AZT is described. Glycosylation of silylated thymine with 2,3,5-tri-O-benzoyl-L-arabinofuranosyl acetate (5) affords the α-nucleoside 7 after debenzoylation. Deoxygenation at C-2′ of the selectively protected 8, followed by displacement of a 3′-methanesulfonyl group by lithium azide leads to the title compound which did not exhibit antiviral activity against HIV-1.

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