SYNTHESIS OF N-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL) AND N-(N,N'-DIACETYLCHITOLBIOSYL) AMIDES OF L-HISTIDINE

The synthesis of N-(2-acetamido-2-deoxy-beta-D-glucopyranosy)- L-histi dine amide (10) and N-(2-acetamido-4-O-(2-acetamido-2-deoxy-beta-D ano syl)-2-deoxy-beta-D-glucopyranosyl)-L-histidine amide (11) is achieved via coupling of ,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosylamine (2 ) and 6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-3-6- di-O-acetyl-2 -deoxy-beta-D-glucopyranosylam (4), respectively, with N-alpha,N-tau-d i-Boc-L-histidine (5) in the presence of 2-ethoxy-1-N-ethoxycarbonyl-1 ,2-dihydroquinoline and subsequent deprotection. Compound 11 is an in hibitor of chitinase from the brine shrimp Artemia salina.