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13C, 15N CP MAS and high resolution multinuclear NMR study of methyl 3,4,6-tri-O-acetyl-2-(3′-arylureido)-2-deoxy-β-d-glucopyranosides

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

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
446 KB
Volume
290
Category
Article
ISSN
0008-6215

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✦ Synopsis

Four new derivatives of methyl 3,4,6-triacetyl-2-deoxy-(3'-arylureido)-fl-D-glucopyranoside were studied by ~H, ~3C, ~SN NMR in CDC13 solutions and by ~3C, ~3N NMR in the solid state. The replacement of one aryl substituent by another has no influence on the proton and carbon chemical shifts within the sugar moiety, in solution. The differences in 13C chemical shifts A = (~liquid --6solid are significant for C-3 (deshielding of -3.4 to -3.8 ppm), C-5 and OMe but not observed for C-2, where the ureido substituent is linked, thus indicating that this fragment of the structure is rigid. The values of A in ~SN chemical shifts of N-3' are -2.3 to -2.8 ppm (increase of shielding in the solids); the effect of replacement of substituent at aromatic ring is larger than the contribution of intermolecular H-bond interaction. The values of 15.5-16.1 Hz for ~Jc-r-N and 21.2-21.5 Hz for ~Jco N indicate that the two C-N-3' bonds are of significant double bond character.

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