Synthesis of a Positional Isomer of Neamine; 5-O-(2, 6-Diacetamido-2, 6-dideoxy-α-D-glucopyranosyl)-N, N'-diacetyl-2-deoxystreptamine

Abstract

The 5-O-(2, 6-diamino-2, 6-dideoxy-α-D-glucopyranosyl)-2-deoxystreptamine derivative and its related compounds were synthesized by a modified Königs-Knorr condensation of 3, 4-di-O-acetyl-2, 6-dideoxy-2-(2', 4'-dinitroanilino)-6-phthalimido-α-D-glucopyranosyl bromide (I) with 4, 6-di-O-acetyl-N, N'-dicarbobenzoxy-2-deoxystreptamine (V) and the corresponding streptamine (XI). The aglycons (V) and (XI) were prepared by selective acetylation of the aminocyclitol derivatives by taking advantage of the reactivity difference between the hydroxyl groups at C₅ and C₄ or C₆. The condensed products were converted to N-acetyl derivatives and were shown to have the α-configuration by PMR spectroscopy.