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Synthesis of 3-Azidopropyl-Functionalized GalNAc-β-(1→4)-Gal Natural Disaccharide

preprint
submitted on 24.10.2019, 15:12 and posted on 28.10.2019, 21:14 by Sebastien Vidal, Dominique Lafont, Shuai Wang
Oligosaccharides such as the GalNAc-β-(1→4)-Gal disaccharide are involved in host-pathogen interactions and their synthesis is a continuing challenge for organic chemists. Only a few reports have discussed the synthesis of functionalized GalNAc-β-(1→4)-Gal for its further conjugation and applications in glycobiology. The synthetic route described here is taking advantage of (1) a simple and affordable GlcNAc donor which is epimerized to the more expensive GalNAc donor and (2) a 1,6-anhydro-galactose acceptor exalting the reactivity at the 4-position of galactose. The allyloxycarbonyl (Alloc) protecting group used at the 2-position of the GalNAc residue was important (1) for a successful epimerization of the GlcNAc residue into the corresponding GalNAc donor but also (2) for the stereoselective β-glycosylation through anchimeric assistance. The key disaccharide intermediate was further transformed to a trichloroacetimidate donor which could then be glycosylated with any alcohol. The example chosen here is the 3-azidopropyl aglycon for the design of multivalent glycoclusters.

Funding

Agence Nationale de la Recherche (ANR-12-BSV5-0020)

History

Email Address of Submitting Author

sebastien.vidal@univ-lyon1.fr

Institution

University Claude Bernanrd Lyon 1

Country

France

ORCID For Submitting Author

0000-0001-7812-698X

Declaration of Conflict of Interest

The authors declare no conflict of interest

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