Iodine monochloride/silver trifluoromethanesulfonate (ICI/AgOTf) as a convenient promoter system for O-glycoside synthesis.
The novel promoter system iodine monochloride/silver trifluoromethanesulfonate (ICl/AgOTf) was evaluated with various thioglycoside donors and saccharide acceptors, and O-glycosides were obtained in 46-82% yield. Several practical advantages of the ICl/AgOTf system over known promoter systems were observed, such as convenient handling of the reagents and absence of byproducts related to N-succinimide.
Ercegovic
T
T
Organic Chemistry, Center for Chemistry and Chemical Engineering, University of Lund, P.O. Box 124, SE-221 00 Lund, Sweden.
Meijer
A
A
Magnusson
G
G
Ellervik
U
U
D002712:Chlorides; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007202:Indicators and Reagents; D007454:Iodides; D007700:Kinetics; D008698:Mesylates; D015394:Molecular Structure
D002712:Chlorides; D006027:Glycosides; D007202:Indicators and Reagents; D007454:Iodides; D008698:Mesylates; C009813:iodine monochloride; C012077:trifluoromethanesulfonic acid