A novel oxidatively removable linker and its application to alpha-selective solid-phase oligosaccharide synthesis on a macroporous polystyrene support

A novel p-acylaminobenzyl-type linker and its application to the solid phas e synthesis of oligosaccharides are described. The p-glutarylaminobenzyl et her of a monosaccharide was readily introduced to a polymer support by amid e bond formation. The linker moiety was smoothly cleaved by DDQ oxidation. alpha-Selective glycosylation was accomplished by virtue of the solvent eff ect of diethyl ether on a solid support of a macroporous polystyrene. High a-selectivity was achieved by the use of benzylated donors possessing the b ulky t-butyldiphenylsilyl group at the 6-position.