Synthesis and NMR study of N,N '-bis(methyl 3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosid-2-yl)urea and its N '-nitroso derivative

N,N'-Bis(methyl 3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosid-2-yl)urea 1 and its N'-nitroso derivative 2 were synthesized from methyl 2-amino-3,4, 6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside and di(4-nitrophenyl)carbamat e. The nitrosation was carried out using N2O3 in dichloromethane. The struc ture of compounds was analyzed by H-1 C-13, N-15 NMR in CDCl3 and C-13 CP M AS in the solid state. The assignments of resonances were done by COSY H-1, C-13, HETCOR and the H-1, N-15 2D correlation spectroscopy. Compound 1 giv es one set of H-1/C-13 resonances in solution, but exhibits polymorphism in the solid state.