Electrochemical synthesis of glycoconjugates of 3I2-hydroxy-I5-steroids by using non-activated sugars and steroidal thioethers

A new protocol for the electrochemical synthesis of glycoconjugates is presented. Thioether derivatives of cholesterol and other sterols were subjected to anodic oxidation in the presence of a sugar alcohol affording glycoconjugates with the sugar linked to a steroid moiety by an ether bond. The iso...

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Published inTetrahedron Vol. 69; no. 42; pp. 8904 - 8913
Main Authors Tomkiel, Aneta, Brzezinski, Krzysztof, Aotowski, Zenon, Siergiejczyk, Leszek, WaAejko, Piotr, Witkowski, StanisAaw, Kowalski, Jan, PAoszyAska, Jolanta, Sobkowiak, Andrzej, Morzycki, Jacek
Format Journal Article
LanguageEnglish
Published 01.10.2013
Subjects
Anodizing
Bonding
Derivatives
Ethers
Steroids
Sterols
Sugars
Synthesis
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Summary:A new protocol for the electrochemical synthesis of glycoconjugates is presented. Thioether derivatives of cholesterol and other sterols were subjected to anodic oxidation in the presence of a sugar alcohol affording glycoconjugates with the sugar linked to a steroid moiety by an ether bond. The isomeric 6I2-3I-,5I--cyclo-steroidal thioethers proved to be better sterol donors than the normal 3I2-I5-steroidal thioethers.
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ISSN:0040-4020
DOI:10.1016/j.tet.2013.07.106