Structure and Reactivity of Glycosides: IV.~1 Koenigs-Knorr Synthesis of Aryl #beta#-D-Glucopyranosides Using Phase-Transfer Catalysts

摘要

A series of acetylated #beta#-D-glucopyranosides were prepared in 12-63% yields from tetra-O-acetyl-#alpha#-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substitutents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols.