Benzeneselenenyl triflate as an activator of thioglycosides for glycosylation reactions.
A new method for the activation of thioglycosides was developed by use of benzeneselenenyl triflate (PhSeOTf), which, upon reaction with either a primary or secondary sugar HO-group, afforded O-glycosides under extremely mild reaction conditions. The reaction was applicable to various l-thiohexosides 2-6 as well as to a 2-thioglycoside 20 derived from N-acetylneuraminic acid (NeuAc).
Ito
Y
Y
RIKEN Institute of Physical and Chemical Research, Saitama, Japan.
Ogawa
T
T
Numata
M
M
Sugimoto
M
M
D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates; D008722:Methods; D008969:Molecular Sequence Data; D016566:Organoselenium Compounds; D013865:Thioglycosides / Q000138:chemical synthesis
D008698:Mesylates; D016566:Organoselenium Compounds; D013865:Thioglycosides; C065936:benzeneselenyl trifalate