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Samarium Diiodide Mediated Reductive Coupling of Epoxides and Carbonyl Compounds: A New Stereocontrolled Synthesis of C-Glycosides from 1,2-Anhydro Sugars

AutorChiara, José Luis ; Sesmillo, Esther
Palabras claveC-glycosides
Electron transfer
Radical reactions
Fecha de publicación30-ago-2002
EditorJohn Wiley & Sons
CitaciónAngewandte Chemie International Edition 41, 17 (2002), pp. 3242-3246
ResumenThe significant advances in the understanding of the biological function of carbohydrates and glycoconjugates achieved during the last two decades have stimulated the development of glycomimetics as fundamental tools for biological research and as potential agents for therapeutic intervention. C-Glycosides are of special relevance in this context due to their resistance to hydrolysis and to their occurrence in a number of natural products with interesting biological activity. Methods for their preparation using anomeric anions, cations, radicals, and carbenes have been extensively studied. 1,2-Anhydro sugars, readily available and well-known donors for the stereoselective preparation of O-glycosides, have also found application in the stereoselective synthesis of C-glycosides.
Versión del editorhttp://dx.doi.org/10.1002/1521-3773(20020902)41:17<3242::AID-ANIE3242>3.0.CO;2-I
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