A Substituent‐Directed Strategy for the Selective Synthesis of L‐Hexoses: An Expeditious Route to L‐Idose,European Journal of Organic Chemistry

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A Substituent‐Directed Strategy for the Selective Synthesis of L‐Hexoses: An Expeditious Route to L‐Idose
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2021-02-02 , DOI: 10.1002/ejoc.202100042
Nicholas W. See ₁ , Norbert Wimmer ₁ , Elizabeth H. Krenske ₁ , Vito Ferro ₂

Affiliation

C‐5 epimerisation via free radical reduction of functionalised D‐hexoses is one of the fastest routes to rare L‐hexoses. With the aid of DFT calculations, we demonstrate that both a β‐F and a C‐6 methoxycarbonyl group installed in a D‐gluco system are key to optimising the stereoselectivity for the L‐ido product. We also present the shortest developed synthetic route to a derivative of L‐idose from a commercially available starting material.

中文翻译：

L-己糖的选择性合成的替代导向策略：加快生产L-Idose的途径

通过自由基还原功能化D-己糖来进行C-5差向异构化是获得稀有L-己糖的最快途径之一。借助DFT计算，我们证明了安装在D-葡萄糖系统中的β-F和C-6甲氧羰基都是优化L-ido产品立体选择性的关键。我们还提出了从商业上可获得的原料到L-idose衍生物的最短开发合成路线。

更新日期：2021-03-08

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