Thiosugars. V. Synthesis of 1-Thio-β-D-ribopyranose and 1-Thio-β-D-mannopyranose Derivatives

Abstract

Crystalline product obtained by the reaction of potassium ethylxanthate upon an anomeric mixture of 2, 3, 4-tri-O-acetyl-D-ribopyranosyl bromides or that of 2, 3, 4, 6-tetra-O-acetyl-D-mannopyranosyl bromides in anhydrous acetone was confirmed to be one anomer of 2, 3, 4-tri-O-acetyl-D-ribopyranosyl ethylxanthates or that of 2, 3, 4, 6-tetra-O-acetyl-D-mannopyranosyl ethylxanthates, respectively. Their anomeric configurations at carbon 1 were assumed to be β. Three derivatives of 1-thio-β-D-ribopyranose and four derivatives of 1-thio-β-D-mannopyranose were synthesized in crystalline forms from acetylated glycosyl ethylxanthates mentioned above.