کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10579900 | 980437 | 2007 | 9 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
New insights into the conformational properties of α-C-glucosides
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی معدنی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
A series of alkyl α-d-C-glucopyranosides were synthesized and their conformational properties analyzed by CD and NMR spectroscopy. The conformational analysis revealed that the hydroxymethyl group populations (torsion angle Ï, O1-C1-C2-O2) and those around the C-glucopyranosidic bond (torsion angle Φ; O2-C6-C7-C8) depend on the structural nature of the C-aglycon. The gt and the exo-syn populations increased as the C-aglycon became more substituted. Linear correlations between these rotational populations and proton chemical shifts versus the Taft's steric parameters revealed the significant role of the C-aglycon in the overall conformation of C-glucosides. The stereoelectronic exo-deoxoanomeric effect, affecting the rotation of the hydroxymethyl group, becomes more important as the steric hindrance of motion increases. A pseudo-anomer rotational comparison study was also performed.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 18, Issue 23, 26 November 2007, Pages 2803-2811
Journal: Tetrahedron: Asymmetry - Volume 18, Issue 23, 26 November 2007, Pages 2803-2811
نویسندگان
Carlos Mayato, Rosa L. Dorta, Jesús T. Vázquez,