Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination
Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination
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可见光介导的还原脱碘作用实现α-连接2-脱氧糖苷的立体选择性合成
DOI：
10.1002/chem.201405516
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发表时间：
2014
期刊：
影响因子：
--
通讯作者：
Wan Q.
中科院分区：
文献类型：
--
作者：
Wang H.;Tao J.;Cai X.;Chen W.;Zhao Y.;Xu Y.;Yao W.;Zeng J.;Wan Q.
2-脱氧糖及其衍生物广泛存在于许多具有重要药用价值的天然产物中。然而，构建特定的2-脱氧-糖苷键仍然是一个挑战。在这里，我们报道了一种有效的方法，通过2-碘-糖基乙酸酯的糖基化和随后的可见光介导的无锡还原脱碘反应来制备2-脱氧-α-糖苷。我们已经成功地应用糖基化后脱碘策略合成了30多个具有良好立体选择性和效率的单、二、三、四和五脱氧糖。该方法还用于合成含四个α键的2-脱氧四糖。
2‐Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2‐deoxy‐glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2‐deoxy‐α‐glycosides by glycosylation of 2‐iodo‐glycosyl acetate and subsequent visible‐light‐mediated tin‐free reductive deiodination. We have successfully applied the postglycosylational‐deiodination strategy in the synthesis of more than 30 mono‐, di‐, tri‐, tetra‐ and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2‐deoxy‐tetrasaccharide containing four α‐linkages.