The 13C NMR Method for Determining the Absolute Configuration of the 1,2-Glycols Consisting of Secondary and Tertiary Hydroxyl Groups

The fucofuranoside method, the 13C NMR method for determining the absolute configuration of secondary alcohols, is applied to five known steroids having a 1,2-glycol group composed of secondary and tertiary hydroxyl groups. The 1,2-alignment of the polar fucofuranosyl and tertiary hydroxyl group was found to have little influence on the requisite conformation of the glycosidic linkage. It showed the normal pattern of the distribution of the ΔδC (and ΔδH) values, as previously observed for simple monohydroxy derivatives, demonstrating the usefulness of the method for this type of compound.