title: Synthesis of glycoaminooxy acid and N-oxyamide-linked glycolipids.
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.
authors.affiliation: PPSM, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France. joanne.xie@ens-cachan.fr.
authors.forename: N
authors.initials: N
authors.lastname: Chen
authors.forename: J
authors.initials: J
authors.lastname: Xie
mesh_terms: D002236:Carbohydrate Conformation; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D010072:Oxamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D006017:Glycolipids; D006027:Glycosides; D010072:Oxamic Acid; C008728:oxamide