Chemical Transformation of Uronic Acids leading to Aminocyclitols. II. Synthesis of Hexaacetyl-streptamine from N-Acetyl-D-glucosamine

Abstract

By employing the oxidative decarboxylation reaction using lead tetraacetate and successive nitromethane cyclization reaction in the reaction sequence, N-acetyl-D-glucosamine (11a) has been converted to hexaacetyl-streptamine (20a) in 8% overall yield. It has been also suggested that the present transformation would provide a versatile method for preparation of aminocyclitols from various types of uronic acids.