The Use of Acetyl Bromide for the Multigram Synthesis of the Anti-HIV Agent 2′,3′-Didehydro-2′,3′-Dideoxycytidine (d4C)
- 1 October 1990
- journal article
- research article
- Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids
- Vol. 9 (7) , 885-897
- https://doi.org/10.1080/07328319008045205
Abstract
Treatment of uridine (1) with acetyl bromide produced bromoacetate 2 which was reduced with Zn/Cu to give the 2′,3′-unsaturated uridine (d4U; 3). Conversion of the uracil moiety of 3 to thioamide 7 with Lawesson's reagent, followed by amination and deprotection with methanolic ammonia, afforded d4C (9). This multigram scale process for the synthesis of d4C proceeded in 20% yield from uridine.This publication has 28 references indexed in Scilit:
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