Synthesis of 3′-deoxy-3′- C-methyl nucleoside derivatives

Abstract

2′,3′-Dideoxy-3′- C-methyl nucleosides bearing the five naturally occurring nucleic acid bases were synthesized. Additionally, the 3′-deoxy-3′- C-methyl nucleoside analogues bearing 5-aminoimidazole-4-carboxamide as well as 1,2,4-triazole-3-carboxamide moieties were prepared. The synthesis of the corresponding 2′,3′-dideoxy-3′- C-methyl triazole derivative was also accomplished. The dideoxynucleoside derivatives were prepared by radical deoxygenation from their 3′-deoxy-3′- C-methyl parent ribonucleosides. When evaluated for their antiviral activity in cell culture experiments, none of these compounds showed any significant antiviral activity.