Synthesis of novel L-2',3'-dideoxy-2'-trifluoromethyl-4'- thiocytidines from alpha-trifluoromethyl-alpha,beta-unsaturated ester

Xingang Zhang; Feng-Ling Qing

doi:10.1021/jo0159690

Synthesis of novel L-2',3'-dideoxy-2'-trifluoromethyl-4'- thiocytidines from alpha-trifluoromethyl-alpha,beta-unsaturated ester

J Org Chem. 2002 Feb 8;67(3):1016-9. doi: 10.1021/jo0159690.

Authors

Xingang Zhang¹, Feng-Ling Qing

Affiliation

¹ Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 11856055
DOI: 10.1021/jo0159690

Abstract

A short and efficient synthesis of L-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidines is described. (2R,4S/2S,4S)-5-(tert-Butyldimethylsiloxy)-2-trifluoromethylpentan-4-olide (3a and 3b) are prepared from alpha-trifluoromethyl-alpha,beta-unsaturated ester (1) in three steps and converted to compounds 6a and 6b. The corresponding 1-O-acetyl derivatives 8a and 8b were obtained via the usual Pummerer rearrangement from 6a and 6b in two steps, which were in turn used to synthesize L-4'-thiocytidines 10a and 10b.