Stereoselective synthesis of 2-deoxy-furanosides from 2,3-anhydro-furanosyl thioglycosides

摘要

The stereocontrolled synthesis of 2-thiotolyl-furanosides from 2,3-anhydro-furanosyl thioglycosides through a rearrangement-glycosylation process is reported. The efficiency of this reaction is high, providing 70-95% yields of the products. Treatment of the resulting 2-deoxy-2thiotolyl-glycosides with hydrogen and Raney nickel affords the corresponding 2-deoxy-furanosides with a 1,3-syn relationship.