Thin-layer and paper chromatography of steroidal β- d-glucopyranosides, β- d-glucopyranosiduronic acids, and derivatives

Abstract

A number of related steroidal β- d-glucopyranoside peracetates, free β- d-glucopyranosides, and β- d-glucopyranosiduronic acids, chiefly in the androstane and pregnane series, were chromatographed on thin layers of silica gel. In all three classes R F differences between members of axial-equatorial pairs were small and, contrary to rule, the equatorially-oriented member frequently was the more mobile. It was not possible to separate mixtures of free glucosides and glucosiduronic acids. Thin-layer chromatography on silica gel remains, however, an excellent method for detecting simple free glucosides. Partition paper chromatography of the free glucosides and glucosiduronic acids gave far better results: reasonable R F differences were obtained for all axial-equatorial pairs, the axially-oriented member of a given pair was the more mobile in all cases, and mixtures of free glucosides and glucosiduronic acids were separated without difficulty.