Asymmetric synthesis of D- and L-2-deoxy-4-thioriboses

Article abstract of DOI:10.1016/S0957-4166(00)80489-9

Both D- and L-enantiomers of 2-deoxy-4-thioribose derivatives 12 and 17 were prepared stereospecifically in 12 steps from 1,3-propanediol. The key intermediary 2,3-epoxy alcohols, 8 and 15 were obtained with high enantiomeric excess by the Sharpless asymmetric epoxidation using (+)-L- diethyl tartrate and (-)-D-diethyl tartrate.