Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*
Open Access
- 1 August 2005
- journal article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 24 (4-6) , 415-424
- https://doi.org/10.1081/car-200066978
Abstract
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.Keywords
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