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Reversing Reactivity: Stereoselective Desulfurative β-O-Glycosylation of Anomeric Thiosugars with Carboxylic Acids Under Copper or Cobalt Catalysis
preprintsubmitted on 20.12.2019, 21:35 and posted on 31.12.2019, 20:37 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.