title: 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.
abstract: The combination of 1-benzenesulfinyl piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf(2)O) forms a new, powerful, metal-free thiophile that can readily activate both armed and disarmed thioglycosides, via glycosyl triflates, in a matter of minutes at -60 degrees C in dichloromethane, in the presence of 2,4,6-tri-tert-butylpyrimidine (TTBP). The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA.
authors.forename: D
authors.initials: D
authors.lastname: Crich
authors.forename: M
authors.initials: M
authors.lastname: Smith
mesh_terms: D000812:Anhydrides / Q000737:chemistry; D002240:Carbohydrate Sequence; D003080:Cold Temperature; D004355:Drug Stability; D006027:Glycosides / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry*; D008969:Molecular Sequence Data; D010880:Piperidines / Q000737:chemistry*; D013441:Sulfinic Acids / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D000812:Anhydrides; D006027:Glycosides; D008698:Mesylates; D010880:Piperidines; D013441:Sulfinic Acids; D013865:Thioglycosides; C425152:benzenesulfinic acid; C012077:trifluoromethanesulfonic acid