Synthesis of glycoaminooxy acid and N-oxyamide-linked glycolipids
1PPSM, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France. joanne.xie@ens-cachan.fr.
Organic & Biomolecular Chemistry
|December 10, 2015
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.
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