S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/trifluoromethanesulfonic anhydride: a convenient system for the generation of glycosyl triflates from thioglycosides.
[structure] The combination of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT, 1) and trifluoromethanesulfonic anhydride forms a powerful, metal-free, thiophile which readily activates thioglycosides, via glycosyl triflates, at -60 degrees C in dichloromethane, in the presence of 2,6-di-tert-butyl-4-methylpyridine. The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity.
Crich
D
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Smith
M
M
D001565:Benzoates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*; D008752:Methylene Chloride / Q000737:chemistry; D012997:Solvents; D013865:Thioglycosides / Q000737:chemistry*
D001565:Benzoates; D008698:Mesylates; D012997:Solvents; D013865:Thioglycosides; C412875:methylamino-2-phenyl-2-butyl-3,4,5-trimethoxybenzoate; D008752:Methylene Chloride; C012077:trifluoromethanesulfonic acid