Deoxysugar Synthesis. II. Deoxygenations of Methyl 2, 6-Dibenzyloxy-carbonylamino-2, 6-dideoxy-α-D-glucopyranoside

Abstract

The 3-p-toluenesulfonate (4) of methyl 2, 6-dibenzyloxycarbonylamino-2, 6-dideoxy-α-D-glucopyranoside was treated with sodium borohydride in dimethyl sulfoxide, giving 3-deoxy-and 4-deoxy-α-D-ribo-hexopyranosides (10 and 11) in a ratio of 1 : 5. On the other hand, analogous treatment of the 4-p-toluenesulfonate (5) afforded the allo-3, 4-epoxide (19). Further, related study was described.