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Crystal structure and solid-state NMR analysis of methyl 2,3,6-tri-O-acetyl-2-deoxy-2-[3-(2-phenylethyl)-ureido]-β-d-glucopyranoside

✍ Scribed by Roma Anulewicz; Iwona Wawer; Bogusława Piekarska-Bartoszewicz; Andrzej Temeriusz

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
437 KB
Volume
281
Category
Article
ISSN
0008-6215

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✦ Synopsis

The X-ray diffraction analysis of methyl 2,3,6-tri-O-acetyl-2-deoxy-2-[3-(2-phenylethyl)-ureido]-beta-D- glucopyranoside has been performed, establishing that molecules are associated by two types of NH...O hydrogen bonds, N-1-H with carbonyl-oxygen and N-3-H with anomeric oxygen, with N...O distances 2.902 and 2.904 A, respectively. The urea moiety of the molecule is in anti Z,Z conformation. The signals in the 13C CP MAS NMR spectrum are neither multiplied nor split, indicating that there is one molecule in the crystal asymmetric unit. The difference in chemical shifts between solid- and liquid-state spectra are significant for C-2 and C-3 of D-glucose moiety (2.3-2.5 ppm) and for NCH2, CH2Ph carbon atoms.

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