A synthesis of 2,2,2-Trichloroethyl 2-Acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside

Abstract

The conversion of 2-acetamido-2-deoxy-D-glucose into 2-acetamido-3,4,6- tri-O-acetyl-2-deoxy-α-D-glucosyl chloride has been reinvestigated and the chloride transformed, with some modification of the literature method, into 2,2,2-trichloroethyl 2-acetamido-4,6-O-benzylidene-2- deoxy-β-D-glucoside. This compound has been converted into the title compound by the sequence acetylation, acid hydrolysis and selective acetylation. An efficient synthesis of benzyl 2,3-di-O-acetyl-β-D- galacto-pyranosideis reported and its unsuccessful selective acetylation contrasted with the above.