The synthesis of 2-amino-2-deoxyhexoses: D-glucosamine, D-mannosamine, D-galactosamine, and D-talosamine

Abstract

Methods for the preparation of the hydrochlorides of 2-amino-2-deoxy-D-glucose (D-glucosamine) and 2-amino-2-deoxy-D-mannose (D-mannosamine) from tri-O-acetyl-D-glucal and of 2-amino-2-deoxy-D-galactose (D-galactosamine) and 2-amino-2-deoxy-D-talose (D-talosamine) from tri-O-acetyl-D-galactal are described. The reactions involve addition of nitrosyl chloride to the acetylated glycal followed by conversion of the adduct to acetylated derivative of the 2-oximinohexose and reduction of the oxime to amine.