Synthesis of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine analogues. n-Butyramide, 3-chloropropionamide, 3-aminopropionamide, and isovaleramide analogues

The syntheses of four analogues of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine are described. Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-β-d-glucopyranosylamine. n-Butyric anhydride gave N-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-3-chloropropionamide. Equilibration of the latter with ammonium bicarbonate gave N1-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-3-aminopropionamide. Succinimidyl isovalerate was synthesized and gave N-(2-acetamido-2-deoxy-β-d-glucopyranosyl)isovaleramide.