文献类型：期刊文献

英文题名：NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides

作者：Liu, Rongkun[1];Hua, Qingting[1];Lou, Qixin[1];Wang, Jiazhe[1];Li, Xiaona[1];Ma, Zhi[1];Yang, You[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

年份：2021

卷号：86

期号：6

起止页码：4763

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20211410168851);WOS:【SCI-EXPANDED(收录号:WOS:000631442900033)，CCR-EXPANDED(收录号:WOS:000631442900033)】；

基金：Financial support from the National Natural Science Foundation of China (21871081 and 22071054) and the Fundamental Research Funds for the Central Universities (50321031916002 and 22221818014) is gratefully acknowledged.

语种：英文

外文关键词：Sugars

摘要：Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biological processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho- hexynylbenzoates is proposed.