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NMR study of methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(alkylureido)-β-D-glucopyranosides

✍ Scribed by Iwona Wawer; Małgorzata Weychert; Jan Klimkiewicz; Bogusława Piekarska-Bartoszewicz; Andrzej Temeriusz

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
117 KB
Volume
37
Category
Article
ISSN
0749-1581

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✦ Synopsis

Five derivatives of methyl 3,4,6-triacetyl-2-deoxy-(3@-dialkylureido)-b-D-glucopyranoside were studied by 1H and 13C, NMR spectroscopy in solutions and by 13C NMR spectroscopy in the solid state. Sterically CDCl 3 crowded substituents such as n-hexyl and cylcohexyl change the chemical shifts of H-1, H-2 and H-3 and also the chemical shifts of C-2 and C-3 of the glucopyranose ring. The low-temperature 1H and 13C spectra showed separate signals of the two alkyl groups, located E and Z with respect to C-2@xO. The barrier to rotation of the fragment is 40.4 kJ mol~1 for the diethyl and 39.2 kJ mol~1 for the di-n-hexyl substituent. The N-3@ÈR 2 (*GE) solid-state 13C NMR spectra indicated that both of the above compounds are polymorphic, exhibiting two to four di †erent forms.

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15N and 1H NMR study of ureido sugars, d
15N and 1H NMR study of ureido sugars, derivatives of 2-amino-2-deoxy-β-D-glucopyranosides
✍ M. Weychert; J. Klimkiewicz; I. Wawer; B.Piekarska-Bartoszewicz; A. Temeriusz 📂 Article 📅 1998 🏛 John Wiley and Sons 🌐 English ⚖ 209 KB 👁 1 views

The 15N NMR spectra of a series of derivatives of 2-amino-2-deoxy-b-D-glucopyranose and dipeptides or secondary amines were recorded. In the dipeptide derivatives the chemical shift of nitrogen atom N-1 (linked to sugar) is essentially unchanged and the shifts of nitrogen atoms N-3 and N-6 are deter