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Title: | Intramolecular 1,8-hydrogen atom transfer. Stereoselectivity of the hexopyranos-5'-yl radical reactions in Hex p-(1→4)-Hex p disaccharide systems |
Authors: | Martín, Ángeles CSIC ORCID ; Pérez-Martín, Inés CSIC ORCID ; Quintanal, Luis M.; Suárez, Ernesto CSIC ORCID | Issue Date: | 9-Sep-2008 | Publisher: | American Chemical Society | Citation: | Journal of Organic Chemistry 73(19): 7710-7720 (2008) | Abstract: | The 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. | Description: | 11 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 | URI: | http://hdl.handle.net/10261/12617 | DOI: | 10.1021/jo801499d | ISSN: | 0022-3263 |
Appears in Collections: | (IPNA) Artículos |
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File | Description | Size | Format | |
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JOC 2008, 73, 7710.pdf | Artículo principal | 1,77 MB | Adobe PDF | ![]() View/Open |
JOC 2008, 73, 7710-SI.pdf | Supporting Information | 3,08 MB | Adobe PDF | ![]() View/Open |
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