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
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
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DOI：
10.1021/ja0111481
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发表时间：
2001-09-19
影响因子：
15
通讯作者：
Smith, M
中科院分区：
文献类型：
--
作者：
Crich, D;Smith, M
1-苯亚砜基胡椒啶（BSP）和三氟甲烷磺酸酐（Tf2O）的结合形成了一种新的、强大的、无金属的亲硫剂，它可以在-60度的温度下，在二氯甲烷中，在2,4,6-三叔丁基嘧啶（TTBP）存在的情况下，通过三氟糖基酸，在几分钟内很容易地激活武装和解除武装的硫糖苷。经醇处理后，三氟化糖基迅速而干净地转化为糖苷，收率高，选择性好。
The combination of 1-benzenesulfinyl piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf2O) 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 degreesC 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.