A `Glycosynthase'-assisted synthesis of some epoxyalkyl beta-C-oligosaccharides

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