Synthesis of a Core Trisaccharide as a Versatile Building Block for N‐Glycans and Glycoconjugates

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Abstract
N‐Linked oligosaccharides from glycoproteins (N‐glycans) can be conveniently assembled with a building block approach. A protected form of the core trisaccharide (β‐mannosyl chitobiose) was identified as a key building block. The chitobiose part of the core trisaccharide was built from a glycosyl fluoride, which served as a precursor for the reducing GlcNAc azide and the inner GlcNAc moiety. β‐Mannosylation was accomplished at the trisaccharide stage by intramolecular inversion of a β‐glucosyl chitobiose. The benzylidene protection of the β‐mannoside and the azido group at the reducing end of the core trisaccharide allow modular synthesis of N‐glycans and their glycoconjugates.