Synthesis of 1-(3'-azido-2',3'-dideoxy-α-L-threo-pentofuranosyl)thymine as a potential anti-HIV agent

Article abstract of DOI:10.1055/s-1991-26543

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.