Preferred Conformation of C-Glykosides. 9. Conformational Analysis of 1,4-Linked Carbon Disaccharides

Article abstract of DOI:10.1021/jo00028a018

The preferred solution conformation of the 1,4-linked carbon disaccharides 3-10 has been determined based on vicinal coupling constants in the 1H NMR spectrum.The conformation of these compounds can be predicted on the basis of the preference of the C-glycosidic bond for the "exo-anomeric" conformation and the diamond lattice analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.The importance of 1,3-diaxial-like interactions has been demonstrated by showing that structural modifications which alter these interactions result in predictable and significant changes in the conformational behavior.The conformational similarity of carbon and oxygen disaccharides has been demonstrated experimentally by a comparison of NOE and T₁ data.