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Intramolecular 1,8‐Hydrogen Abstraction Between Glucopyranose Units in a Disaccharide Model Promoted by Alkoxy Radicals
Author(s) -
Francisco Cosme G.,
Herrera Antonio J.,
Kennedy Alan R.,
Melián Daniel,
Suárez Ernesto
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020301)41:5<856::aid-anie856>3.0.co;2-f
Subject(s) - chemistry , hydrogen atom abstraction , alkoxy group , radical , disaccharide , regioselectivity , intramolecular force , abstraction , benzene , medicinal chemistry , derivative (finance) , stereochemistry , computational chemistry , organic chemistry , catalysis , philosophy , alkyl , epistemology , financial economics , economics
A nine‐membered transition state characterizes the regioselective abstraction of the proton at C 5′ that leads to the orthoacetate 2 as the product. The alkoxy radical intermediate is obtained from the Glc‐ α 1→4‐Glc derivative 1 with (diacetoxyiodo)benzene (DIB) and iodine. A similar 1,8‐hydrogen abstraction results when the alkoxy radical intermediate is generated under reductive conditions.