Synthesis p. 683 - 686 (1991)
Update date:2022-08-05
Topics:
Czernecki
Le Diguarher
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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Doi:10.1139/v73-573
(1973)Doi:10.3390/molecules161210292
(2011)Doi:10.1016/0040-4039(88)85068-8
(1988)Doi:10.1021/ja206050b
(2011)Doi:10.1016/0022-328X(90)80080-J
(1990)Doi:10.1021/jo00009a014
(1991)