Synthesis of 2′-Fluoro and 2′,4′-Dimethyl Pyrimidine C-Nucleoside Analogues as Potential Anti-HCV Agents

Abstract

Stereoselective synthesis of novel 2′-fluoro and 2′,4′-dimethyl carbocyclic pyrimidine C-nucleoside analogues using selective fluorination of an epoxide opening reaction is described. The key fluorinated intermediate 7 was prepared from the epoxide intermediate 5 via selective ring opening of the epoxide. Synthesis of isonucleosidic bases through the mesylate 7 and final deprotection provided the target carbocyclic pyrimidine C-nucleoside analogues. The synthesized compounds 15 and 18 were evaluated as inhibitors of the hepatitis C virus (HCV) in the Huh-7 cell line in vitro.