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dc.contributor.authorMartín, Ángelesen_US
dc.contributor.authorQuintanal, Luis M.en_US
dc.contributor.authorSuárez, Ernesto-
dc.date.accessioned2009-05-12T06:16:25Z-
dc.date.available2009-05-12T06:16:25Z-
dc.date.issued2007-06-05en_US
dc.identifier.citationTetrahedron Letters 48(31): 5507-5511 (2007)en_US
dc.identifier.issn0040-4039-
dc.identifier.urihttp://hdl.handle.net/10261/12978-
dc.description5 pages, 3 schemes.-- Printed version published Jul 30, 2007.-
dc.descriptionExperimental procedures and analytical data for all new compounds are provided. Supplementary data (24 pages) available at: http://dx.doi.org/10.1016/j.tetlet.2007.05.166-
dc.description.abstractThe regioselectivity of the hydrogen atom transfer (HAT) reaction promoted by alkoxyl radicals generated from 3-hydroxypropyl α-d-mannopyranoside derivative (O-glycoside) and 2,6-anhydro-d-glycero-d-manno-decitol derivative (C-glycoside) is studied. The O-glycoside model abstracts preferentially the hydrogen atom at C-5 (1,8-HAT) while the C-glycoside abstracts the hydrogen atom at C-1 (1,6-HAT) but no abstraction at C-5 could be detected. These results are explained by the stereoelectronic control exerted by the exo-anomeric effect in the O-glycoside.-
dc.description.sponsorshipThis work was supported by the Investigation Programmes Nos. CTQ2004-06381/BQU and CTQ2004-02367/BQU of the Ministerio de Educación y Ciencia, Spain, cofinanced by the Fondo Europeo de Desarrollo Regional (FEDER). L.M.Q. thanks the Program I3P-CSIC, for a fellowship.-
dc.format.extent2373 bytes-
dc.format.extent137639 bytes-
dc.format.mimetypetext/plain-
dc.format.mimetypeapplication/pdf-
dc.language.isoengen_US
dc.publisherElsevier-
dc.rightsclosedAccessen_US
dc.titleHydrogen atom transfer experiments provide chemical evidence for the conformational differences between C- and O-glycosidesen_US
dc.typeartículoen_US
dc.identifier.doi10.1016/j.tetlet.2007.05.166-
dc.relation.publisherversionhttp://dx.doi.org/10.1016/j.tetlet.2007.05.166-
dc.contributor.funderMinisterio de Educación y Ciencia (España)-
dc.contributor.funderEuropean Commission-
dc.contributor.funderConsejo Superior de Investigaciones Científicas (España)-
dc.identifier.funderhttp://dx.doi.org/10.13039/501100000780es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100003339es_ES
dc.type.coarhttp://purl.org/coar/resource_type/c_6501es_ES
item.cerifentitytypePublications-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.grantfulltextnone-
item.openairetypeartículo-
item.fulltextNo Fulltext-
item.languageiso639-1en-
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