Selective cleavage of ester type glycoside-linkages and its application to structure determination of natural oligoglycosides

On treatment with anhydrous LiI, 2,6-lutidine and anhydrous methanol, an ester type glycosyl linkage of acidic tri- and di-terpenes was selectively cleaved without decomposition of a reducing terminal of the resulting sugar moiety to give an anomeric mixture of methyl glycosides along with an aglycone or a pro-aglycone in quantitative yield. In this reaction, no hydrolysis of any other glycoside linkages took place.