Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate.
Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completely stereoselective with respect to both sugar and steroid but only partially regioselective - primary and anomeric hydroxyl groups in sugars were the most reactive ones while no substantial differences in reactivity was found for different secondary hydroxyl groups.
Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland.
Aneta M
AM
Tomkiel
Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland.
Leszek
L
Siergiejczyk
Faculty of Chemistry, Rzeszów University of Technology, P. O. Box 85, 35-959 Rzeszów, Poland.
Dorota
D
Naróg
Faculty of Chemistry, Rzeszów University of Technology, P. O. Box 85, 35-959 Rzeszów, Poland.
Jolanta
J
Płoszyńska
Faculty of Chemistry, Rzeszów University of Technology, P. O. Box 85, 35-959 Rzeszów, Poland.
Andrzej
A
Sobkowiak
Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland. Electronic address: morzycki@uwb.edu.pl.
Jacek W
JW
Morzycki
D002784:Cholesterol / Q000737:chemistry* / Q000378:metabolism*; D004563:Electrochemistry / Q000379:methods*; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
D002784:Cholesterol
Cholesterol; Cholesteryl diphenylphosphate; Cholesterylation; Electrochemical oxidation; Glycosylation