The synthesis of 2'-deoxythymidine derivatives and the cycloaddition route to 2'-deoxy-O-glycosidic linkages.

Title: The synthesis of 2'-deoxythymidine derivatives and the cycloaddition route to 2'-deoxy-O-glycosidic linkages.
Identifier: AAI9720092
identifier: 9720092
Creator: Geer, Aloma B.
Contributor: Adviser: Richard W. Franck
Date: 1997
Language: English
Publisher: City University of New York.
Subject: Chemistry, Organic
Abstract: Part 1. The synthesis of 2{dollar}\sp\prime{dollar}-deoxy-2{dollar}\sp\prime{dollar}-thiothymidine derivatives was accomplished by utilizing both tolyl(bistolylthio)sulfonium salt and dimethyl(methylthio)sulfonium salt as the electrophilic reagent in the glycosyl transfer of ribal derivatives and bis-silylated thymine. The effect of the size of the C-3 blocking group, the temperature of the reaction, and the polarity of solvent on the facial selectivity of the sulfonium species was investigated.;Part 2. A novel method for the construction of the 2{dollar}\sp\prime{dollar}-deoxy-O-glycosidic linkage was developed. Our approach involved an inverse electron demand Diels-Alder reaction between sugar dienophiles and a thione diene. The facial selectivity of the cycloaddition was dependent on the stereochemistry of the substituents of the glycals and on the choice of solvent. The below facial cycloadduct, upon exposure to Raney Nickel provided the 2-deoxy-O-{dollar}\alpha{dollar}-disaccharide.
Type: dissertation
Source: PQT Legacy CUNY.xlsx
degree: Ph.D.

Media: The synthesis of 2'-deoxythymidine derivatives and the cycloaddition route to 2'-deoxy-O-glycosidic linkages.