Generation of Glycosyl Radicals from Glycosyl Sulfoxides and Its Use in the Synthesis of C-linked Glycoconjugates
Generation of Glycosyl Radicals from Glycosyl Sulfoxides and Its Use in the Synthesis of C-linked Glycoconjugates
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从糖基亚砜生成糖基自由基及其在 C-连接糖复合物合成中的应用
DOI：
10.1002/anie.202009828
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Niu Dawen
中科院分区：
文献类型：
--
作者：
Shang Weidong;Su Sheng-Nan;Shi Rong;Mou Ze-Dong;Yu Guo-Qiang;Zhang Xia;Niu Dawen
我们在这里报告糖基亚砜附加芳基碘部分作为容易获得的，空气和水分稳定的前体糖基自由基。这些糖基亚砜可以通过快速有效的分子内自由基取代事件转化为糖基自由基。使用这种类型的前体能够在温和的条件下合成各种复杂的C -连接糖缀合物。该反应可以在水性介质中进行，并且适合于糖肽模拟物和碳水化合物-DNA缀合物的合成。
We here report glycosyl sulfoxides appended with an aryl iodide moiety as readily available, air and moisture stable precursors to glycosyl radicals. These glycosyl sulfoxides could be converted to glycosyl radicals by way of a rapid and efficient intramolecular radical substitution event. The use of this type of precursors enabled the synthesis of various complex C -linked glycoconjugates under mild conditions. This reaction could be performed in aqueous media and is amenable to the synthesis of glycopeptidomimetics and carbohydrate-DNA conjugates.