C-Aryl Glycosylation via Interrupted Pummerer Rearrangement†,Chinese Journal of Chemistry

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C-Aryl Glycosylation via Interrupted Pummerer Rearrangement†
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2023-07-06 , DOI: 10.1002/cjoc.202300308
Jiagen Li ₁ , Xuefeng Jiang _{1,

2,

3}

Affiliation

C-aryl glycosides are an important kind of carbohydrate derivatives for drug discovery, due to their distinctive attributes of resistance to hydrolysis from enzymes. Herein, C-aryl glycosylation was established for the synthesis of 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process, featured with sulfonium-tethered [3,3]-sigmatropic rearrangement between sulfoxide glycals and phenols. This protocol offers a broad substrate scope with diverse glycosyl and phenols. Dapagliflozin, Empagliflozin, and Ipragliflozin analogs were straightforward achieved, respectively.

中文翻译：

通过中断的 Pummerer 重排进行 C-芳基糖基化†

C-芳基糖苷由于其独特的抗酶水解特性，是药物发现中重要的碳水化合物衍生物。在此，建立了通过间断Pummerer法合成2-硫C-芳基糖醛和1,2-二氢苯并呋喃稠合C-芳基糖苷的C-芳基糖基化，其特征在于锍系链的[3,3 ] -σ重排亚砜糖醛和酚类。该实验方案提供了具有多种糖基和酚类的广泛底物范围。达格列净、恩格列净和伊格列净类似物分别是直接实现的。

更新日期：2023-07-06

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