Intramolecular 1,8-Hydrogen Abstraction Between Glucopyranose Units in a Disaccharide Model Promoted by Alkoxy Radicals

Abstract

A nine-membered transition state characterizes the regioselective abstraction of the proton at C5′ that leads to the orthoacetate 2 as the product. The alkoxy radical intermediate is obtained from the Glc-α1→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. Supporting information for this article is available on the WWW under http://www.angewandte.com or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.