A highly efficient synthetic strategy for polymeric support synthesis of Le(x), Le(y), and H-type 2 oligosaccharides

The O-protecting groups Levulinoyl (Lev) and 9-fluroenylmethoxycarbonyl (Fmoc) offer an attractive set of orthogonal protecting groups which are compatible with base sensitive N-trichloroethoxylcarbonyl (Troc) group. B exploiting these orthogonal protecting groups and a novel phenolic ester linker, a series of oligosaccharide of biological importance, Le(x), H-type 2, and Le(y), were synthesized on the polytheylene glycol resin MPEG (Mw 5000). The products bearing a p-hydroxybenzyl group could be easily converted into glycosyl donors for further synthesis. Using this strategy, a spacer containing tumor antigen Le(y)-Lac hexasaccharide was described. The artificial spacer at the reducing end provides an opportunity for selective conjugation to an appropriate carrier protein for immunlogical studies.