Hydrogen atom transfer experiments provide chemical evidence for the conformational differences between C- and O-glycosides |
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| Authors: | Angeles Martí n |
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| Affiliation: | Instituto de Productos Naturales y Agrobiología del C.S.I.C., Carretera de La Esperanza 3, 38206 La Laguna, Tenerife, Spain |
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| Abstract: | The 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. |
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