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Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature.

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.

SUBMITTER: Liu Y

PROVIDER: S-EPMC9037310 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature.

Liu Yao Y Yu Xiao-Bing XB Zhang Xiang-Mei XM Zhong Qian Q Liao Li-Hua LH Yan Nan N

RSC advances 20210804 43

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 ...[more]

PMID: 35479995

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