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Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides |
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| Authors: | Ugo Chiacchio Maria Grazia Saita Giuseppe Gumina Venerando Pistarà Anna Piperno |
| Institution: | a Dipartimento di Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy b Department of Pharmaceutical Science, Medical University of S. Carolina, 280 Calhoun Street, Charleston, SC 29425, USA c Dipartimento Farmaco-Chimico, Università di Messina, Viale SS. Annunziata, 98168 Messina, Italy d Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-300 Leuven, Belgium |
| Abstract: | The enantioselective synthesis of homocarbocyclic-2′oxo-3′-azanucleosides has been performed by cycloaddition reaction of the N-glycosyl nitrones with allyl nucleobases. The use of nitrones originated from two different carbohydrates, the N-ribosyl nitrone and the N-mannosyl nitrone, proceeded in a stereocontrolled and predictable manner with a good degree of enantioselectivity, so allowing an easy entry to both enantiomers. |
| Keywords: | Nucleosides 1 3-Dipolar cycloaddition N-Glycosyl nitrones |
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