Collect. Czech. Chem. Commun. 2002, 67, 1267-1276

Synthesis of 2',3'-Dideoxy-2'-trifluoromethyl-N-azanucleosides

Feng-Ling Qinga,*, Jiang Yub and Xiang-Kai Fub

a College of Chemistry and Chemical Engineering, Donghua University, 1882 West Yanan Lu, Shanghai 200051, China
b College of Chemistry and Chemical Engineering, Southwest Normal University, Beibei, Chongqing, 400715, China


The trifluoromethylation of (Z)/(E)-tert-butyl (4S)-4-(2'-ethoxycarbonyl-2'-bromoprop-1'-enyl)-2,2-dimethyloxazolidine-3-carboxylate (4), which is derived from chiral serine aldehyde, yields α-trifluoromethyl-α,β-unsaturated ester 1. Compound 1 is used as a key intermediate for the synthesis of a number of 2',3'-dideoxy-2'-trifluoromethyl-N-azanucleosides.

Keywords: Trifluoromethylation; α-Trifluoromethyl-α,β-unsaturated ester; Nucleosides; Azanucleosides; Aminosugars; Antivirals; Fluorinated compounds.

References: 30 live references.