Abstract
To address the medicinal chemists need for new synthetic methods for the preparation of unnatural carbohydrates, a new de novo method for carbohydrate synthesis has been developed. These routes use a palladium catalyzed glycosylation reaction to stereoselectively control the anomeric center and subsequent diastereoselective post glycosylation to install the remaining sugar stereocenters. The utility of this method was demonstrated by the syntheses and biological evaluation of several digitoxin oligosaccharide analogues.
Keywords: De Novo Synthesis, Carbohydrate Synthesis, Oligosaccharide Synthesis, Unnatural Sugars, Digitoxin, Antitumor Agent, Cardiac Glycoside, Palladium-Catalyzed Glycosylation
Current Topics in Medicinal Chemistry
Title: The De Novo Synthesis of Oligosaccharides: Application to the Medicinal Chemistry SAR-Study of Digitoxin
Volume: 8 Issue: 2
Author(s): George O'Doherty and Maoquan Zhou
Affiliation:
Keywords: De Novo Synthesis, Carbohydrate Synthesis, Oligosaccharide Synthesis, Unnatural Sugars, Digitoxin, Antitumor Agent, Cardiac Glycoside, Palladium-Catalyzed Glycosylation
Abstract: To address the medicinal chemists need for new synthetic methods for the preparation of unnatural carbohydrates, a new de novo method for carbohydrate synthesis has been developed. These routes use a palladium catalyzed glycosylation reaction to stereoselectively control the anomeric center and subsequent diastereoselective post glycosylation to install the remaining sugar stereocenters. The utility of this method was demonstrated by the syntheses and biological evaluation of several digitoxin oligosaccharide analogues.
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Cite this article as:
O'Doherty George and Zhou Maoquan, The De Novo Synthesis of Oligosaccharides: Application to the Medicinal Chemistry SAR-Study of Digitoxin, Current Topics in Medicinal Chemistry 2008; 8 (2) . https://dx.doi.org/10.2174/156802608783378828
DOI https://dx.doi.org/10.2174/156802608783378828 |
Print ISSN 1568-0266 |
Publisher Name Bentham Science Publisher |
Online ISSN 1873-4294 |
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