Synthesis of an N-glycan decasaccharide of the hybrid type

A hybrid-type N-glycan decasaccharide GlcNAcMan7GlcNAc2 was synthesized from the pentasaccharide GlcNAcMan2GlcNAc2 as an advanced intermediate and an acyl-protected pentamannosyl donor. Benzyl mannoside was regioselectively benzoylated and glycosylated at OH-3 and OH-6 with a dimannoside to give the 3,6-branched pentamannoside. Coupling of the two pentasaccharides furnished the target decasaccharide in 60% yield. Deprotection of the base labile functions furnished a hybrid-type N-glycan decasaccharide functionalized for the conjugation with peptides or proteins.