1-苯亚磺酰基哌啶及其类似物的改进合成方法，用于与三氟甲磺酸酐联合活化硫代糖苷
IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE.
作者信息
Crich David, Banerjee Abhisek, Li Wenju, Yao Qingjia
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
出版信息
J Carbohydr Chem. 2005;24(4-6):415-424. doi: 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.
摘要
描述了一种用于大规模生产1-苯亚磺酰基哌啶和其他亚磺酰胺的改进方案。结果表明，在三氟甲磺酸酐介导的硫代糖苷活化反应中，1-苯亚磺酰基吡咯烷和N,N-二乙基苯亚磺酰胺与1-苯亚磺酰基哌啶具有类似的功能，并且它们较低的结晶性使其能够在-78°C下使用，而1-苯亚磺酰基哌啶需要在-60°C才能保持溶解状态。N,N-二环己基苯亚磺酰胺与三氟甲磺酸酐组合时不能活化硫代糖苷，这归因于其较大的空间位阻。
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