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Solid-Phase Synthesis of Complex Oligosaccharides Using A Novel Capping Reagent

Journal of Organic Chemistry, ISSN: 0022-3263, Vol: 69, Issue: 6, Page: 1853-1857
2004
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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.

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