Highly chemo- and stereoselective glycosidation of permethacrylated O-glycosyl trichloroacetimidate reagents promoted by TMSNTf2 |
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Authors: | Christelle Zandanel |
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Institution: | University of Strasbourg, Faculty of Pharmacy CNRS/UMR 7199, Laboratory of Functional ChemoSystems, 74 route du Rhin BP 60024, 67 401 Illkirch, France |
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Abstract: | TMSNTf2 has been used efficiently as a promoter in glycosidation reaction involving permethacrylated Schmidt reagents. While TMSNTf2 is known to be a powerful activator for CO double bonds, we have discovered that this reagent can activate CN double bond selectively, even in the presence of excess CO groups of permethacrylated O-glycosyl trichloroacetimidate substrates. Glycosides are synthesized in moderate to reasonable yields with an excellent overall β-stereoselectivity. |
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