Studies on d-Glucosamine Derivatives. XII. The Synthesis of N-Acetyi-3-O- and -4-O-aminoacyl-d-glucosamines

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Abstract
As a part of the investigation of the stabilities of the esters between N-acetyl-d-glucosamine and various amino acids, N-acetyl-3-O- and 4-O-aminoacyl-d-glucosamines were synthesized. Benzyl N-acetyl-4, 6-O-benzylidene-α- and -β-d-glucosaminide, and benzyl N-acetyl-3-O-benzyl-6-O-trityl-α- and -β-d-glucosaminide were condensed with N-benzyloxycarbonyl-amino acids by the dicyclohexylcarbodiimide method, followed by the step-by-step removal of the protecting groups. The α-Glycosidic benzyl group, however, could not be removed by the catalytic hydrogenolysis in the presence of oxalic acid, probably because of a steric hindrance.