IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE.
An improved protocol for the large scale production of 1-benzenesulfinyl piperidine and other sulfinamides is described. It is demonstrated that 1-benzenesulfinyl pyrrolidine and N,N-diethyl benzenesulfinamide function analogously to 1-benzenesulfinyl piperidine in the trifluoromethanesulfonic anhydride-mediated activation of thioglycosides, and that their less crystalline nature enables them to be used at -78 °C as opposed to the -60 °C required to keep 1-benzenesulfinyl piperidine in solution. N,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride which is attributed to its greater steric bulk.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Banerjee
Abhisek
A
Li
Wenju
W
Yao
Qingjia
Q