Synthesis of 2,6-Dideoxy-4-S-Methyl-4-Thio-D-ribo-Hexopyranose, A Component of the Esperamicin Oligosaccharide

Article abstract of DOI:10.1016/0040-4020(95)00059-H

Two synthetic approaches to 2,6-dideoxy-4-S-methyl-4-thio-D-ribo pyranose, a component of the oligosaccharide of esperamicins are described.An asymmetric synthesis, starting from the propargylic alcohol dimer, relies on the Sharpless asymmetric epoxidation and the regioselective opening of epoxy alcohols.The other synthesis is based on stereocontrolled transformations of a readily available sugar precursor, D-galactose.