Solid-phase supported mimic of GDP-l-galactose

A C-glycoside mimetic of l-galactose 1-diphosphate, a potential ligand of GDP-l-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated l-fucose, by periodate-osmium tetroxide degradation of the double bond, by condensation of the obtained aldehydes with benzylacetate and by deprotection. The obtained mimetic was linked to a sepharose resin.