Collect. Czech. Chem. Commun.
2005, 70, 2086-2100
https://doi.org/10.1135/cccc20052086
Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides
Ondřej Vícha, Ladislav Kniežoa,*, Hana Dvořákováb, Ivan Raicha and Štěpán Valentaa
a Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b NMR Laboratory, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
Abstract
Conformational behavior of two C-disaccharides, containing D-glucopyranose moiety at the non-reducing end and L- or D-2-deoxy-arabino-hexopyranose moiety at the reducing end, has been studied using MM3 calculations and NMR experiments. The obtained results show that the conformational preference around the C-glycosidic bond is the same in both compounds and corresponds with the exo-anomeric effect. On the other hand, both compounds differ markedly in the conformational arrangement around the C-aglycone bond where the population of conformers is controlled by 1,3-diaxial-like interactions.
Keywords: Carbohydrates; C-Glycosides; C-Disaccharides; Conformational analysis; NMR spectroscopy; MM3 calculations.
References: 33 live references.
