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Título: | Synthesis of highly condensed polycyclic carbohydrates by reaction of a spirocyclic enamino sulfonate derived from D-xylofuranose with bifunctional reagents |
Autor: | Cordeiro, Alessandra CSIC; Jimeno, M. Luisa CSIC ORCID; Maestro, Miguel A.; Camarasa Rius, María José CSIC ORCID; Quesada, Ernesto CSIC ORCID ; San-Félix, Ana CSIC ORCID | Fecha de publicación: | 2007 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 72 : 9713-9721 (2007) | Resumen: | The appropriately substituted 5-O-tosyl derivative (1), easily prepared from 1,2-O-isopropylidene-R-D- xylofuranose, serves as a useful precursor for the preparation of highly condensed cyclic carbohydrates. The synthesis involves a first cyclization of the 5-O-tosyl sugar derivative 1 to a highly reactive cyclic enamine, which subsequently undergoes the nucleophilic attack of a bifunctional reagent X(CH2)nZina regio-and stereospecific way. Finally, a spontaneous cyclization step allows the formation of a stereochemically defined extra ring, fused to the sugar backbone. The functionalization and size of this ring can be varied by the proper choice of the bifunctional reagent. X-ray diffraction analysis and intensive NMR studies with one of these carbohydrates were performed to highlight the strained nature of these compounds. | Versión del editor: | http://dx.doi.org/10.1021/jo701775a | URI: | http://hdl.handle.net/10261/34535 | DOI: | 10.1021/jo701775a | ISSN: | 0022-3263 |
Aparece en las colecciones: | (CENQUIOR) Artículos |
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