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Hydrogen atom transfer experiments provide chemical evidence for the conformational differences between C- and O-glycosides

AuthorsMartín, Ángeles ; Quintanal, Luis M.; Suárez, Ernesto
Issue Date5-Jun-2007
CitationTetrahedron Letters 48(31): 5507-5511 (2007)
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.
Description5 pages, 3 schemes.-- Printed version published Jul 30, 2007.
Experimental 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
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2007.05.166
Appears in Collections:(IPNA) Artículos
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