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Título: | Intramolecular 1,8-hydrogen-atom transfer reactions in (1-->4)-O-disaccharide systems: conformational and stereochemical requirements |
Autor: | Francisco, Cosme G. CSIC; Herrera, Antonio J. CSIC ; Kennedy, Alan R.; Martín, Ángeles CSIC ORCID ; Melián, Daniel CSIC; Pérez-Martín, Inés CSIC ORCID ; Quintanal, Luis M. CSIC; Suárez, Ernesto CSIC ORCID | Palabras clave: | Carbohydrates Disaccharides Esters Radical reactions Trioxocane |
Fecha de publicación: | 1-oct-2008 | Editor: | John Wiley & Sons | Citación: | Chemistry - A European Journal 14(33): 10369-10381 (2008) | Resumen: | The stereochemical and conformational factors controlling the intramolecular hydrogen-atom transfer (HAT) reaction between the two pyranose units in a (1-->4)-O-disaccharide when promoted by a primary 6-O-yl radical are studied. Models with α-D-Glcp-(1-->4)-β-D-Glcp, α-L-Rhamp-(1-->4)-α-D-Galp or α-D-Manp-(1-->4)-β-L-Gulp skeletons led exclusively to the abstraction of the hydrogen from H--C-5' and the formation, through a nine-membered transition state, of a 1,3,5-trioxocane ring system in a stable boat-chair conformation. Notwithstanding, derivatives of α-L-Rhamp-(1-->4)-α-D-Glcp or α-D-Manp-(1-->4)-α-D-Galp exclusively abstract the hydrogen from H--C-1' through a seven-membered transition state and, therefore, lead to an interglycosidic spiro ortho ester. | Descripción: | 13 pages, 1 figure, 1 table, 7 schemes.-- PMID: 18830990 [PubMed]. Supporting information (30 pages) available at: http://www3.interscience.wiley.com/journal/121427980/suppinfo |
Versión del editor: | http://dx.doi.org/10.1002/chem.200801414 | URI: | http://hdl.handle.net/10261/12604 | DOI: | 10.1002/chem.200801414 | ISSN: | 0947-6539 |
Aparece en las colecciones: | (IPNA) Artículos |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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Chem EurJ. 2008, 14, 10369.pdf | Artículo principal | 2,01 MB | Adobe PDF | Visualizar/Abrir |
Chem EurJ. 2008, 14, 10369-SI.pdf | Supporting Information | 1,37 MB | Adobe PDF | Visualizar/Abrir |
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