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

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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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The article was received on 12 Nov 2015, accepted on 27 Nov 2015 and first published on 27 Nov 2015

Article type: Paper
DOI: 10.1039/C5OB02328A
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Org. Biomol. Chem., 2016,14, 1102-1110

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    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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