Synthesis of 3'-deoxy-4'-thionucleosides

Abstract

The racemic synthesis of 3'-deoxy-4'-thionucleosides, which are of interest as potential antiviral and antitumor drug candidates, was achieved. A key reaction involved a tandem intra-and intermolecular S N 2 reaction of a thioepoxide for constructing a 3'-deoxy-4'thioribose skeleton. Pummerer reaction and subsequent Vorbrüggen-type glycosylation furnished 3'-deoxy-4'-thionucleosides. The proposed method is applicable for enantioselective synthesis using a commercially available chiral oxirane derivative. S B OH HO S OCOAr RO X OCOAr S OMs X = H, OAc 3'-Deoxy-4'-thionucleoside RO