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Intramolecular 1,8-Versus 1,6-Hydrogen Atom Transfer between Pyranose Units in a (1→4)-Disaccharide Model Promoted by Alkoxyl Radicals. Conformational and Stereochemical Requirements

AutorMartín, Ángeles ; Pérez-Martín, Inés ; Quintanal, Luis M.; Suárez, Ernesto
Fecha de publicación4-abr-2007
EditorAmerican Chemical Society
CitaciónOrganic Letters 9(9): 1785-1788 (2007)
ResumenThe stereochemical and conformational factors controlling the intramolecular hydrogen atom transfer (HAT) reaction between the two pyranose units in a (1→4)-disaccharide when promoted by a primary 6-O-yl radical are studied. Models with α-d-Glcp-(1→4)-β-d-Glcp or α-l-Rhamp-(1→4)-α-d-Galp skeletons lead exclusively to the abstraction of 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 abstract exclusively H−C-1' through a seven-membered transition state and therefore lead to an interglycosidic spiro ortho ester.
Descripción4 pages, 1 table, 3 schemes.-- Printed version published Apr 26, 2007.
Supporting information (complete description of experimental details and product characterization) available at: http://pubs.acs.org/doi/suppl/10.1021/ol070496q
Versión del editorhttp://dx.doi.org/10.1021/ol070496q
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