A 'Glycosynthase'-assisted Synthesis of Some Epoxyalkyl β-C-Oligosaccharides

Abstract

A series of alkenyl β-D-C-glucopyranosides has been glycosylated with α-D-glucopyranosyl fluoride in a ‘Glycosynthase’ reaction to yield a range of alkenyl β-C-cellobiosides and -triosides and in one case a -C-cellotetraoside. Conversion of some of the alkenyl β -D-C-oligosaccharide products into their corresponding epoxides and subsequent deprotection under standard conditions have afforded a panel of epoxyalkyl β -C-oligosaccharides for evaluation as inhibitors of retaining β-glycan hydrolases.