Syntheses of the anti-AIDS drug 2', 3'-dideoxycytidine from cytidine

PS Manchand, PS Belica, MJ Holman…

Index: Manchand; Belica; Holman; Huang; Maehr; Tam; Yang Journal of Organic Chemistry, 1992 , vol. 57, # 12 p. 3473 - 3478

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Citation Number: 34

Abstract

Two efficient synthesea of the anti-AIDS drug 2 ', 3'-dideoxycytidine (3) from N '- acetylcytidine (4) are described. In one, silylation of the C-5'hydroxyl group of 4 with tert- butyldimethylsilyl chloride followed by treatment with 1', 1'-(thiocarbony1) diimidazole gave the cyclic thionocarbonate 7, which on reaction with l, &dimethyld-phenyl-l, 3- diazaphospholidine gave the crystalline alkene 8. Hydrogenation of 8, followed by ...