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Issue 3, 2016
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Synthesis of glycoaminooxy acid and N-oxyamide-linked glycolipids

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Abstract

Aminooxyl sugar derivatives are versatile building blocks for the generation of various glycoconjugates with interesting bioactivities. We report herein a synthetic method for the preparation of orthogonally protected glycoaminooxy acid from methyl α-D-glycopyranoside in 7 steps. The key steps involve the selective protection, O-alkylation and Mitsunobu reaction. Fully deprotected N-oxyamide-linked novel glycolipids can be easily generated from the glycoaminooxy ester or from the 2-hydroxy free sugar in 5 or 6 steps.

Graphical abstract: Synthesis of glycoaminooxy acid and N-oxyamide-linked glycolipids

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Supplementary files

Article information


Submitted
12 Nov 2015
Accepted
27 Nov 2015
First published
27 Nov 2015

Org. Biomol. Chem., 2016,14, 1102-1110
Article type
Paper
Author version available

Synthesis of glycoaminooxy acid and N-oxyamide-linked glycolipids

N. Chen and J. Xie, Org. Biomol. Chem., 2016, 14, 1102
DOI: 10.1039/C5OB02328A

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