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Synthesis of Reversed C‐Acyl Glycosides through Ni/Photoredox Dual Catalysis
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-04-17 , DOI: 10.1002/anie.201800701
Shorouk O Badir 1 , Audrey Dumoulin 1 , Jennifer K Matsui 1 , Gary A Molander 1
Affiliation  

The incorporation of C‐glycosides in drug design has become a routine practice for medicinal chemists. These naturally occurring building blocks exhibit attractive pharmaceutical profiles, and have become an important target of synthetic efforts in recent decades.1 Described herein is a practical, scalable, and versatile route for the synthesis of non‐anomeric and unexploited C‐acyl glycosides through a Ni/photoredox dual catalytic system. By utilizing an organic photocatalyst, a range of glycosyl‐based radicals are generated and efficiently coupled with highly functionalized carboxylic acids at room temperature. Distinctive features of this transformation include its mild conditions, impressive compatibility with a wide array of functional groups, and most significantly, preservation of the anomeric carbon: a handle for further, late‐stage derivatization.

中文翻译:

Ni/光氧化还原双催化合成反C-酰基糖苷

在药物设计中加入C-糖苷已成为药物化学家的常规做法。这些天然存在的结构单元表现出有吸引力的药物特性,并已成为近几十年来合成工作的重要目标。1本文描述的是一种通过 Ni/光氧化还原双催化系统合成非异头和未开发的C-酰基糖苷的实用、可扩展且通用的路线。通过利用有机光催化剂,可以产生一系列糖基自由基,并在室温下与高度功能化的羧酸有效偶联。这种转化的显着特征包括其温和的条件、与多种官能团的令人印象深刻的相容性,以及最重要的是,保留了异头碳:为进一步的后期衍生化提供了手段。
更新日期:2018-04-17
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