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Título: | Rigid Spacer-Mediated Synthesis of Bis-Spiroketal Ring Systems: Stereoselective Synthesis of Nonsymmetrical Spiro Disaccharides |
Autor: | Rubio Castillo, Enrique Miguel CSIC; García Moreno, María Isabel; Balbuena Olivia, Patricia; Ortiz-Mellet, Carmen; García Fernández, José Manuel CSIC ORCID | Palabras clave: | Carbohydrates Disaccharides Molecular structure Spiro compounds Caramels Xylylene |
Fecha de publicación: | 25-ene-2005 | Editor: | American Chemical Society | Citación: | Organic Letters 7(4): 729-731 (2005) | Resumen: | The application of the "rigid spacer-mediated linkage between nonreacting centers" concept to the preparation of nonsymmetrical bis-spiroketal structures is demonstrated by the stereoselective synthesis of the bis-spiro fructodisaccharide 1, a minor component of industrial caramels. An o-xylylene bridge has been used to limit the conformational space during the intramolecular glycosylation-spirocyclization reaction of a difructopyranose precursor, thus controlling both the ring size and the stereochemistry at the spiro centers. | Descripción: | 3 páginas, 1 figura, 2 esquemas. | Versión del editor: | http://dx.doi.org/10.1021/ol0474094 | URI: | http://hdl.handle.net/10261/37655 | DOI: | 10.1021/ol0474094 | ISSN: | 1523-7060 |
Aparece en las colecciones: | (IIQ) Artículos |
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