Carbohydrate sulfonyl chlorides for simple, convenient access to glycoconjugates.
[reaction: see text] 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.
Kvaernø
Lisbet
L
Laboratorium für Organische Chemie, ETH Hönggerberg HCI H335, CH-8093 Zürich, Switzerland.
Werder
Moritz
M
Hauser
Helmut
H
Carreira
Erick M
EM
D000924:Anticholesteremic Agents / Q000138:chemical synthesis*; D001384:Azetidines / Q000138:chemical synthesis* / Q000494:pharmacology; D002625:Chemistry, Organic / Q000379:methods*; D020650:Combinatorial Chemistry Techniques; D000069438:Ezetimibe; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D013441:Sulfinic Acids / Q000737:chemistry*
D000924:Anticholesteremic Agents; D001384:Azetidines; D006001:Glycoconjugates; D013441:Sulfinic Acids; C044255:sulfonyl chloride; D000069438:Ezetimibe