Synthetic Studies on Carbohydrate Antibiotics

Part VIII Synthesis of Kanosaminide and Related α-Aminoglucosides

Abstract

The four kinds of aminoglycosides of 2-deoxystreptamine (DSTA)* including kano-saminide were synthesized by a modified Königs-Knorr reaction using a benzylhalogeno derivative of the corresponding aminosugar. Each of the glycosides was isolated as its crystalline N-acetate and proved to have α-configuration. The possible intermediates of this versatile a-glucosylation reaction are discussed.