Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride–diethyl ether as catalyst

Abstract

Stereospecific formation of aryl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides was achieved by reaction of penta-O-acetyl-β-D-glucose 1 with substituted phenols in the presence of boron trifluoride. Yields of the purified products varied from 52–85%. Benzyl alcohol could also be glucosylated using similar conditions. All products were purified by crystallization from ethanol. The purity and the anomeric configuration of the products were determined by means of ¹H and ¹³C NMR spectroscopy, melting points and optical rotation.