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Carbohydrate Sulfonyl Chlorides for Simple, Convenient Access to Glycoconjugates

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journal contribution
posted on 17.03.2005, 00:00 by Moritz Werder, Helmut Hauser, Erick M. Carreira
The use of carbohydrate sulfonyl chlorides is introduced as a new, facile glycoconjugation method which could find broad applications. We demonstrate the approach by synthesizing a number of glycosylated cholesterol absorption inhibitors which display high inhibitory efficacies in our recently established in vitro assay. Furthermore, we highlight an advantage of the electron-withdrawing nature of the sulfonyl linkage which allowed the synthesis of otherwise unstable azetidine conjugates.