A linker for solid phase carbohydrate synthesis, permitting the introduction of variable anomeric functionality in the release step

Article abstract of DOI:10.1016/S0040-4039(98)00312-8

The novel linker methyl 2-(4-methoxycarbonylbutyldimethylsilyl)ethanol (3) was synthesized in 58% overall yield over four steps, starting from 2- (hexenyldimethylsilyl)ethanol. Galactopyranosylation of 3 and coupling of the resulting linker galactoside to aminomethylated polystyrene resin gave a material that could be efficiently de-O-benzoylated as well as O- propionylated. Treatment of the resin with acetic or propionic anhydride in the presence of BF₃·OEt₂ gave the corresponding 1-O-propionyl or -acetyl galactopyranoses.