Abstract
Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The β-mannosidic linkage was created by C-2 epimerization of the initially introduced β- d-gluco-unit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride.
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