Dimethylformamide-Modulated Kdo Glycosylation for Stereoselective Synthesis of α-Kdo Glycosides.,Organic Letters

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Dimethylformamide-Modulated Kdo Glycosylation for Stereoselective Synthesis of α-Kdo Glycosides.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-09 , DOI: 10.1021/acs.orglett.9b04509
Qixin Lou ₁ , Qingting Hua ₁ , Liangliang Zhang ₁ , You Yang ₁

Affiliation

A simple and direct DMF-modulated α-selective Kdo glycosylation approach for the stereoselective synthesis of the α-linked Kdo glycosides is developed. Glycosylation of the readily available peracetylated Kdo ortho-hexynylbenzoate with common acceptor alcohols using SPhosAuNTf2 as a promoter and DMF as a modulating molecule afforded a range of Kdo glycosides with good α-selectivities. Furthermore, the present method is effectively applied in the latent-active synthesis of the α-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 α-selective Kdo glycosylation.

中文翻译：

二甲基甲酰胺调节的Kdo糖基化立体选择性合成α-Kdo糖苷。

开发了一种简单而直接的DMF调节的α-选择性Kdo糖基化方法，用于α-连接的Kdo糖苷的立体选择性合成。使用SPhosAuNTf2作为促进剂和DMF作为调节分子，用常见的受体醇对容易获得的全乙酰化Kdo邻己炔基苯甲酸酯进行糖基化，得到了一系列具有良好α选择性的Kdo糖苷。此外，本发明方法有效地应用于潜在地合成在还原端带有连接子的α-连接的二-Kdo糖苷。最后，在低温NMR中对Kdo亚胺离子的首次观察为DMF调节的α-选择性Kdo糖基化的合理机理提供了证据。

更新日期：2020-01-10

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