ChemInform Abstract: Synthesis of N-(2-Acetamido-2-deoxy-β-D-glucopyranosyl) and N-(N, N′-Diacetylchitobiosyl) Amides of L-Histidine

The synthesis of N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-histidine amide (10) and N-(2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl)-L-histidine amide (11) is achieved via coupling of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosylamine (2) and 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosylamine (4), respectively, with N α ,N τ -di-Boc-L-histidine (5) in the presence of 2-ethoxy-1-N-ethoxycarbonyl-1,2-dihydroquinoline and subsequent deproteotion. Compound 11 is an inhibitor of chitinase from the brine shrimp Artemia salina