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Intramolecular 1,8-hydrogen atom transfer. Stereoselectivity of the hexopyranos-5'-yl radical reactions in Hex p-(1→4)-Hex p disaccharide systems

AuthorsMartín, Ángeles ; Pérez-Martín, Inés ; Quintanal, Luis M.; Suárez, Ernesto
Issue Date9-Sep-2008
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 73(19): 7710-7720 (2008)
AbstractThe stereoselective reduction of hexopyranos-5′-yl radicals in α-d-Hexp-(1→4)-d-Hexp disaccharide models is described. These radicals are generated from a 6-O-yl radical located in the other monosaccharic unit through a 1,8-hydrogen atom transfer. The reaction, which is strongly influenced by steric and stereoelectronic effects, permits in some cases the transformation of α-d-Hexp-(1→4)-d-Hexp into β-l-Hexp-(1→4)-d-Hexp disaccharides in a single step with high diastereoselectivity.
Description11 pages, 5 schemes.-- PMID: 18778104 [PubMed].-- Printed version published Oct 3, 2008.
Supporting Information Available: A complete description of experimental details of precursors and copies of NMR spectra for all new compounds available at: http://pubs.acs.org/doi/suppl/10.1021/jo801499d
Publisher version (URL)http://dx.doi.org/10.1021/jo801499d
Appears in Collections:(IPNA) Artículos
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