Stereoselective synthesis of 2-deoxy-furanosides from 2,3-anhydro-furanosyl thioglycosides.
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-2-thiotolyl-glycosides with hydrogen and Raney nickel affords the corresponding 2-deoxy-furanosides with a 1,3-syn relationship.
Hou
Dianjie
D
Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Lowary
Todd L
TL