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Reversing Reactivity: Stereoselective Desulfurative β-O-Glycosylation of Anomeric Thiosugars with Carboxylic Acids Under Copper or Cobalt Catalysis

preprint
submitted on 20.12.2019 and posted on 31.12.2019 by Samir Messaoudi, Nedjwa Bennai, Amelie Chabrier, Maha Fatthalla, Expédite Yen-Pon, Christine Tran, Mohamed belkadi, Mouad Alami, Laurence Grimaud
We have discovered a new mode of reactivity of 1-thiosugars in the presence of Cu(II) or Co(II) for a stereoselective O-glycosylation reaction. The process involves the use of a catalytic amount of Cu(acac)2 or Co(acac)2 and Ag2CO3 as an oxidant in α,α,α-trifluorotoluene (TFT). Moreover, this protocol turned out to have a broad scope, allowing to prepare a wide range of com-plex substituted O-glycoside esters in good to excellent yields with an exclusive β-selectivity. The late-stage modification of phar-maceuticals by this method was also demonstrated.

History

Email Address of Submitting Author

samir.messaoudi@u-psud.fr

Institution

Université Paris-Saclay, CNRS

Country

France

ORCID For Submitting Author

0000-0002-4994-9001

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version V1

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