Novel inverse-electron-demand cycloadditions for functionalizing carbohydrates.

Title: Novel inverse-electron-demand cycloadditions for functionalizing carbohydrates.
Identifier: AAI9917672
identifier: 9917672
Creator: Li, Baoqing.
Contributor: Adviser: Richard W. Franck
Date: 1999
Language: English
Publisher: City University of New York.
Subject: Chemistry, Organic | Chemistry, Pharmaceutical
Abstract: Two sorts of carbohydrate linkages have been prepared by using novel inverse-electron-demand cycloadditions. Our generalized glycosidation method for introducing oxygen and nitrogen to the anomeric carbon demonstrated an alternative approach to a variety of interesting 2-deoxy-O and 2-deoxy-N glycosides e.g. 4.67 which exist in many natural products, such as aureolic acids 2.23 and glycopeptides 3.2. The stereoselectivity of the cycloadducts 2.48, 4.59, and 4.61 can be controlled by choosing the suitable sugar-based dienophiles (e.g. tri-O-benzyl-D-glucal 1.15 and tri-O-benzyl-D-allal 1.17). Also, the assignment of the stereoselectivity of the cycloadduct 4.46 was based on the analysis of 1D, 2DNMR, and X-ray crystallography.
Type: dissertation
Source: PQT Legacy CUNY.xlsx
degree: Ph.D.

Media: Novel inverse-electron-demand cycloadditions for functionalizing carbohydrates.