Rapid glycosylations under extremely mild acidic conditions. Use of ammonium salts to activate glycosyl phosphites via P-protonation.
Trifluoromethanesulfonic acid salts of tertiary amines were employed as extremely mild acidic activators for rapid glycosylations. Glycosyl phosphite triesters bearing an acid-labile 4,4'-dimethoxytrityl (DMTr) group for transient protection worked as glycosyl donors effectively in the presence of the activators to afford the corresponding disaccharides in good yields without loss of the DMTr group.
Matsumura
Fumiko
F
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, 5-1-5 Kashiwanoha, Kashiwa, Chiba, Japan.
Tatsumi
Shiro
S
Oka
Natsuhisa
N
Wada
Takeshi
T
D006031:Glycosylation; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D017905:Phosphites / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D011522:Protons; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry
D017905:Phosphites; D011522:Protons; D000644:Quaternary Ammonium Compounds; D012492:Salts; D010758:Phosphorus