Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/199514
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Title

Intramolecular 1,8-Hydrogen Atom Transfer Reactions in Disaccharide Systems Containing Furanose Units

AuthorsGuyenne, Sabrina CSIC; León, Elisa I. CSIC ORCID ; Martín, Ángeles CSIC ORCID ; Pérez-Martín, Inés CSIC ORCID ; Suárez, Ernesto CSIC ORCID
KeywordsAlcohols
Reaction products
Mixtures
Conformation
Molecular structure
Issue Date1-Aug-2012
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 77(17): 7371-7391 (2012)
AbstractA previously developed 1,8-hydrogen atom transfer (HAT) reaction promoted by 6-O-yl alkoxyl radicals between the two pyranose units in Hexp-(1→4)-Hexp disaccharides has been extended to other systems containing at least a furanose ring in their structures. In Penf-(1→3)-Penf (A) and Hexp-(1→3)-Penf (B) disaccharides, the 1,8-HAT reaction and concomitant cyclization to a 1,3,5-trioxocane ring are in competition with radical β-scission of the C4–C5 bond and formation of dehomologated products. The influence of the stereoelectronic β-oxygen effect on the β-scission and consequently on the 1,8-HAT reaction has been studied using the four possible isomeric d-furanoses. d-xylo- and d-lyxo-derivatives afforded preferentially 1,8-HAT products, whereas d-arabino- and d-ribo-derivatives gave exclusively direct β-scission of the alkoxyl radical. When the 6-O-yl radical is on a pyranose ring, as occurs in Penf-(1→4)-Hexp (C), it has been shown to provide the cyclized products exclusively.
Publisher version (URL)https://doi.org/10.1021/jo301153u
URIhttp://hdl.handle.net/10261/199514
DOI10.1021/jo301153u
Identifiersissn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IPNA) Artículos




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