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Intramolecular 1,8-Hydrogen Atom Transfer. Stereoselectivity of the Hexopyranos-5'-yl Radical Reactions in Hexp-(1?)-Hexp Disaccharide Systems.

  作者 Martin, Angeles;Perez-Martin, Ines;Quintanal, Luis M.;Suarez, Ernesto;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-19;  页码  7710-7720  
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[摘要]The stereoselective redn. of hexopyranos-5'-yl radicals in a-D-Hexp-(1?)-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 a-D-Hexp-(1?)-D-Hexp into b-L-Hexp-(1?)-D-Hexp disaccharides in a single step with high diastereoselectivity.

 
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