Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature |
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| Authors: | Yao Liu Xiao-Bing Yu Xiang-Mei Zhang Qian Zhong Li-Hua Liao Nan Yan |
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| Affiliation: | National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022 P. R. China.; College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022 P. R. China, |
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| Abstract: | A mild, convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presented via arynes generated in situ combined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction conditions tolerate a variety of the pentoses and hexoses, and the reaction also performs smoothly on protected monosaccharides and disaccharides.We have developed a convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides in good to excellent yields via the arynes generated in situ combined with glycosyl thiols. |
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