Noval Method for the Synthesis of 2', 3'-Unsaturated Nucleosides from 2'(3')-Acetoxy-3'(2')-halogeno Derivatives by Using Sodium Dithionite with Viologen as a Reductive Elimination Mediator

Abstract

Reductive elimination of vicinal acetylated halohydrins with Na₂S₂O₄ as the reducing agent and viologen as the reduction mediator in a two-phase water-organic system is described. 2', 3'-Unsaturated nucleosides such as 1-(5-O-acetyl-2, 3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine, -hypoxanthine and uracil were obtained from 2'(3')-acetoxy-3'(2')-halogeno derivatives in good yields by meanes of this procedure.