Synthesis of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine analogues: Succinamide, l-2-hydroxysuccinamide, and l-2-hydroxysuccinamic acid hydrazide analogues Original Research Article

The syntheses of three analogues of N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-asparagine are described. N-(2-Acetamido-2-deoxy-β-d-glucopyranosyl)succinamide was synthesized by the reaction of pentafluorophenyl succinamate with 2-acetamido-2-deoxy-β-d-glucopyranosylamine. 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucopyranosylamine was synthesized, and the complete assignment of the 1H NMR spectrum is given. Reaction of the protected β-d-glycosylamine with l-malic acid chloralid in the presence of a coupling agent (EEDQ) gave N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucopyranosyl)-l-malamic acid chloralid that was deprotected two ways: (1) using ammonia, which gave N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-2-hydroxysuccinamide, and (2) using hydrazine, which gave N4-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-2-hydroxysuccinamic acid hydrazide.