Synthesis of novel D-2′-Deoxy-2′-C-difluoromethylene-4′-thiocytidine as a potential antitumor agent

Abstract

(formula presented) 2′-Deoxy-2′-C-difluoromethylene-4′-thiocytidine (4) as a potential antitumor agent was synthesized starting from L-xylose via 2-deoxy-2-C-difluoromethylene-4-thiosugar as a key intermediate. An elimination product, 8, was always formed as the major product during removal of the protecting groups under acidic or basic conditions. However, utilizing neutral reaction conditions to remove the protecting groups afforded the desired product 4 exclusively.