Synthesis and solid state 13C and 1H NMR analysis of new oxamide derivatives of methyl 2-amino-2-deoxy-α-d-glucopyranoside and ester of amino acids or dipeptides

The syntheses of new oxamide derivatives of methyl 2-amino-2-deoxy-α-d-glucopyranoside and amino acid or peptide esters are presented. The reaction of methyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-d-glucopyranoside and oxalyl chloride gave N-(methyl 3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosid-2-yl) oxamic acid chloride which on reaction with the ester of Gly, l-Ala, l-Phe, GlyGly, Gly-l-Phe and Gly-l-Ala afforded N-(methyl 3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosid-2-yl), N′-oxalyl-amino acid or dipeptide esters. The structure of the oxamides was studied using 1H, 13C NMR in solution and solid state.