Stereoselective Syntheses of α-d- and β-d-Ribofuranosides Catalyzed by the Combined Use of Silver Salts and Their Partners

Abstract

Abstract α-d-Ribofuranosides are stereoselectively synthesized in high yields from 2,3,5-tri-O-benzyl-1-O-iodoacetyl-d-ribofuranose (1) and trimethylsilylated nucleophiles by the use of silver salts in the coexistence of 3 molar amounts of lithium perchlorate, while β-d-ribofuranosides are prepared predominantly in high yields by the reaction of 1 and trimethylsilylated nucleophiles or 2,3,5-tri-O-benzyl-d-ribofuranose and free alcohols by using [diphenyltin sulfide/silver salt] or [Lawesson’s reagent/silver salt] combined catalyst system.