Journal of Organic Chemistry 2004-03-19

Solid-phase synthesis of complex oligosaccharides using a novel capping reagent.

Xiangyang Wu, Richard R Schmidt

Index: J. Org. Chem. 69(6) , 1853-7, (2004)

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Abstract

Solid-phase-supported oligosaccharide synthesis of a core N-glycan tetrasaccharide and of a trisaccharide containing the Galili antigen is reported. The synthesis is based on a hydroxymethylbenzyl benzoate spacer-linker system attached to the Merrifield resin, O-Fmoc-protected O-glycosyl trichloroacetimidates as glycosyl donors, and benzoyl isocyanate as a capping reagent for low-reactivity hydroxy groups. In this way, the target molecules could be efficiently obtained with little byproduct formation, and hence final purification was convenient.