Tetrahedron

Electrochemical synthesis of glycoconjugates of 3β-hydroxy-Δ 5-steroids by using non-activated sugars and steroidal thioethers

…, K Brzezinski, Z Łotowski, L Siergiejczyk, P Wałejko…

Index: Tomkiel, Aneta M.; Brzezinski, Krzysztof; Lotowski, Zenon; Siergiejczyk, Leszek; Walejko, Piotr; Witkowski, Stanislaw; Kowalski, Jan; Ploszynska, Jolanta; Sobkowiak, Andrzej; Morzycki, Jacek W. Tetrahedron, 2013 , vol. 69, # 42 p. 8904 - 8913

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Citation Number: 8

Abstract

Abstract 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 6β-3α, 5α-cyclo-steroidal thioethers proved to be better sterol donors than the normal 3β-Δ 5-steroidal thioethers.