Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides
2005 ◽
Vol 70
(12)
◽
pp. 2086-2100
◽
Keyword(s):
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.