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The De Novo Synthesis of Oligosaccharides: Application to the Medicinal Chemistry SAR-Study of Digitoxin

[ Vol. 8 , Issue. 2 ]

Author(s):

George O'Doherty and Maoquan Zhou   Pages 114 - 125 ( 12 )

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

Affiliation:

Department of Chemistry,West Virginia University, Morgantown, West Virginia 26506, USA.



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