(13)C-N.M.R. SPECTROSCOPY OF α- AND β-ANOMERIC SERIES OF ALKYL L-ARABINOPYRANOSIDES

Article abstract of DOI:10.1016/S0008-6215(00)85187-3

Anomeric pairs of L-arabinopyranosides of variety of a aliphatic alcohols, were prepared, and their n.m.r. spectroscopy, especially the glycosylation shift of their (13)C signals, was investigated in comparison with those of D-glucopyranosides, D-mannopyranosides, and L-rhamnopyranosides reported previously.It was found that the glycosylation shift of the L-arabinopyranosides in the present study is almost the same as that of D-glucopyranosides, and the conformational equilibrium of each of these L-arabinopyranosides is very similar to that of the corresponding anomer of methyl L-arabinopyranoside, namely, a preponderance of the ⁴C₁ form, regardless of the structure of the aglycon alcohol.The present results are also useful for structural study of naturally occurring arabinopyranosides.