Chemical Transformation of Uronic Acids leading to Aminocyclitols. IV. Synthesis of Hexaacetyl-streptamine from N-Acetyl-D-glucosamine by Means of Electrolytic Decarboxylation

Abstract

Through a short series of reactions (catalytic oxidation, electrolytic decarboxylation, cyclization with alkaline nitromethane, and reduction), a conversion of N-acetyl-D-glucosamine (1) into hexaacetyl-streptamine (6) has been accomplished without previous protection of the hydroxyl groups in the starting compound (1), although the overall yield was not fully satisfactory. The conversion may represent a new and widely applicable means for the synthesis of diaminocyclitols from amino-sugars. A β-methoxyethoxymethyl ether function was unaffected during the anodic oxidation.