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Synthesis of glycoaminooxy acid and N-oxyamide-linked glycolipids

Chen, N; Xie, J ORGANIC & BIOMOLECULAR CHEMISTRYS 2016, 14, 1102-1110.

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 alpha-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.

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Publication

Dates :

Paru le 21 janvier 2016

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DOI: 10.1039/c5ob02328a