For the purpose of the development of modern procedures of glycoside-chemistry, a number of anomeric pairs of D-glucopyranosides, D-mannopyranosides, L-rhamnopyranosides and L-arabinopyranosides of a variety of aliphatic alcohols and carboxylic acids were synthesized. For these glycosides together with the known natural glycosides, carbon signal displacements of both aglycone- and sugar-moieties on glycoside formation, "glycosylation shift" were studied. The exceptional glycosylation shifts for glycosides of relatively hindered aglycone alcohols and carboxylic acids as well as 2-linked glycosides were discussed under the stereochemical consideration. It was also revealed that 13C-nuclear magnetic resonance spectrometry is a valuable tool for the determination of anomeric configuration of mannosides and rhamnosides. In the application of these results, structures of a number of dammarane-saponins of Ginseng and the related Panax species, natural sweet glycosides and glycoside of oriental medicinal plants have been elucidated.
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OSAMU TANAKA (1985) studied this question.