文献类型：期刊文献

英文题名：Dimethylformamide-Modulated Kdo Glycosylation for Stereoselective Synthesis of α-Kdo Glycosides

作者：Lou, Qixin[1];Hua, Qingting[1];Zhang, Liangliang[1];Yang, You[1]

机构：[1]East China Univ Sci & Technol, Shanghai, Peoples R China

年份：2020

卷号：22

期号：3

起止页码：981

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000513082700044)】；

基金：Financial support from the National Natural Science Foundation of China (21871081), the National Thousand Young Talents Program (Y100-4Q1701, YC0140103), and the Fundamental Research Funds for the Central Universities (50321031916002, 22221818014) is gratefully acknowledged.

语种：英文

摘要：A simple and direct DMF-modulated alpha-selective Kdo glycosylation approach for the stereoselective synthesis of the alpha-linked Kdo glycosides is developed. Glycosylation of the readily available peracetylated Kdo ortho-hexynylbenzoate with common acceptor alcohols using SPhosAuNTf(2) as a promoter and DMF as a modulating molecule afforded a range of Kdo glycosides with good alpha-selectivities. Furthermore, the present method is effectively applied in the latent-active synthesis of the alpha-linked di-Kdo glycoside bearing a linker at the reducing end. Finally, the first observation of a Kdo imidinium ion in the low-temperature NMR provides evidence for the plausible mechanism of the DMF-modulated a-selective Kdo glycosylation.