Intramolecular Nitrogen Delivery for the Synthesis of C-Glycosphingolipids. Application to the C-Glycoside of the Immunostimulant KRN7000
Intramolecular Nitrogen Delivery for the Synthesis of C-Glycosphingolipids. Application to the C-Glycoside of the Immunostimulant KRN7000
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DOI：
10.1021/ol5002686
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发表时间：
2014-02
期刊：
影响因子：
5.2
通讯作者：
Ahmad S Altiti;D. Mootoo
中科院分区：
文献类型：
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作者：
Ahmad S Altiti;D. Mootoo
在这种合成C-鞘糖脂的方法中，关键反应是糖连接的高烯丙基碳硫代亚胺酸酯的立体选择性碘环化反应。E型和Z型反应底物通过烯烃复分解策略以汇聚的方式组装，并且在碘环化反应中表现出相同的烯烃面选择性，而与烯烃的几何构型无关，尽管发现E型烯烃的反应活性较低。
The key reaction in this approach to C-glycosphingolipids is the stereoselective iodocyclization of a sugar-linked homoallylic carbonimidothioate. E and Z reaction substrates were assembled in a convergent fashion via an alkene metathesis strategy and exhibited the same alkene facial selectivity in the iodocyclization irrespective of alkene geometry, although the E alkene was found to be less reactive.