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.
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.
Crich
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D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA.
Smith
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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*
D000812:Anhydrides; D006027:Glycosides; D008698:Mesylates; D010880:Piperidines; D013441:Sulfinic Acids; D013865:Thioglycosides; C425152:benzenesulfinic acid; C012077:trifluoromethanesulfonic acid