Stereochemical study of the CD spectral differences between anomers of alkyl glucopyranosides

Article abstract of DOI:10.1016/S0957-4166(98)00037-8

Slightly different chair conformation geometries were demonstrated to be the origin of the C-D spectral differences observed in anomers of alkyl glucopyranosides. The study, using methyl glucopyranoside derivatives as model compounds, showed excellent agreement between CD data, ¹H NMR data, and semiempirical calculations, and the geometries found explained satisfactorily the higher amplitudes observed for the β-anomers of tetrachromophorically substituted alkyl glucopyranosides. The pairwise interactions involving the chromophore at C2, the 2/3, 2/4 and 2/6, were the most dependent on the anomeric configuration, the 2/4 interaction even showing opposite CD signs for the anomers. In addition, the 2/3 pairwise interaction was revealed to be independent of the structural nature of the aglycon.