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

A nine‐membered transition state characterizes the regioselective ion 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 ion results...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2002-03, Vol.41 (5), p.856-858
Main Authors: Francisco, Cosme G., Herrera, Antonio J., Kennedy, Alan R., Melián, Daniel, Suárez, Ernesto
Format: Article
Language:English
Subjects:
Alcohols - chemistry
carbohydrates
conformation analysis
Disaccharides - chemistry
Glucose - chemistry
glycosides
Heparin - analogs & derivatives
hydrogen transfer
Oxidation-Reduction
radical reactions
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A nine‐membered transition state characterizes the regioselective ion 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 ion results when the alkoxy radical intermediate is generated under reductive conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020301)41:5<856::AID-ANIE856>3.0.CO;2-F