Reaction of cholesterol with acetylated alkyl orthoacetates of D-glucopyranose

Summary The condensation of acetylated alkyl orthoacetates of D-glucose with cholesterol has been studied. It has been shown that either transesterification or glycosylation may take place, according to the reaction conditions. Conditions have been found under which the sole direction of the reaction is glycosylation, leading to the 1, 2-trans-glycoside. A standard method for glycosylating complex alcohols with sugar orthoesters has been proposed.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 6–12, 1966