Aminosugars. XVII. Synthesis of Benzyl 2-Acetamino-2-deoxy-α-d-glucopyranosiduronic Acidamides and N-(2-Acetamino-2-deoxy-d-glucuronyl)-aminoacids

Benzyl 2-acetamino-2-deoxy-α-d-glucopyranosiduronic acid was obtained by direct oxidation of the corresponding glucoside, and converted to esters (methyl, ethyl and benzyl) and amides (methyl, ethyl, phenyl and benzyl). Condensation of the uronic acid with aminoacid benzyl-esters (gly, l-ala, l-asp, and l-glu) by dicyclohexylcarbodiimide gave the corresponding amides, some of which were hydrogenated to N-(2-acetamino-2-deoxy-d-glucuronyl)-aminoacids. Acid hydrolysis of the peptides were examined.