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Abstract
By means of a modified Königs-Knorr reaction using 2,3,4,6-tetra-O-benzyl-D-gluco- pyranosyl chloride, all the possible isomers of d-glucopyranoside of trans-2-aminocyclo- hexanol were synthesized. The total yield of the α-anomers exceeded that of the corresponding β-anomers.
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 I-O-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 α-configuration.