CRYSTAL-STRUCTURE AND SOLID-STATE NMR ANALYSIS OF N-(METHYL EOXY-BETA-D-GLUCOPYRANOSIDE)-N'-CARBAMOYL-D-VALINE ETHYL-ESTER

The X-ray diffraction analysis of N-(methyl eoxy-beta-D-glucopyranosid e)-N'-carbamoyl-D-valine ethyl ester has been performed establishing t hat molecules are associated by two types of NH...O hydrogen bonds. Th e N-1-H forms an intermolecular hydrogen bond with carbonyl oxygen, an d the N-3-H forms a hydrogen bond with the anomeric oxygen, with dista nces 2.927(6) Angstrom and 3.063(7) Angstrom, respectively. The urea m oiety of the molecule is in the anti-Z,Z conformation. The signals in the C-13 CP MAS NMR spectrum are neither multiplied nor split, confirm ing that there is one molecule in the crystal asymmetric unit. The dif ference in chemical shifts between solid and solution spectra are sign ificant for C-2, C-3 and OMe group of D-glucose moiety (1.7, 2.6 and 2 .9 ppm respectively) and for NCON, C alpha and C beta D-valine carbon atoms.