Electrochemical synthesis of glycoconjugates from activated sterol derivatives

[Display omitted] •A series of cholesterol donors for electrochemical reactions were prepared.•Electrooxidation of sterol derivatives in presence of a sugar afforded sterol glycoconjugates.•Sterol trichloroacetimidates, diphenylphosphates, and dimethylphosphites were found to be the best sterol donors. Several derivatives of cholesterol and other 3β-hydroxy-Δ5-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors.