title: Rapid glycosylations under extremely mild acidic conditions. Use of ammonium salts to activate glycosyl phosphites via P-protonation.
abstract: 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.
authors.affiliation: Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, 5-1-5 Kashiwanoha, Kashiwa, Chiba, Japan.
authors.forename: Fumiko
authors.initials: F
authors.lastname: Matsumura
authors.forename: Shiro
authors.initials: S
authors.lastname: Tatsumi
authors.forename: Natsuhisa
authors.initials: N
authors.lastname: Oka
authors.forename: Takeshi
authors.initials: T
authors.lastname: Wada
mesh_terms: 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
chemical_list: D017905:Phosphites; D011522:Protons; D000644:Quaternary Ammonium Compounds; D012492:Salts; D010758:Phosphorus