Synthetic Studies on Carbohydrate Antibiotics

Part V. Synthesis of 6-Acetamido-2, 3, 4-tri-O-benzyl-6-deoxy-D-glucopyranos Chloride and Its Use in Königs-Knorr Reaction

抄録

Treatment of methyl tri-O-acetyl-6-azido-6-deoxy-D-glucopyranoside (II) with benzyl chloride afforded the corresponding tri-O-benzyl derivative. Reduction of the azido group with zinc-acetic acid or sodium amalgam gave 6-amino derivative. N-Acetylation, hydrolysis of the 1-0-methyl group, acetylation and treatment with dry hydrogen chloride in dioxane afforded the title compound (VIII). Königs-Knorr reaction of the chloride with (+)- and (-)-2-aminocyclohexanol produced the corresponding glycosides, one of which was proved to have the a-configuration.