Stability of Boronic Esters to Hydrolysis: A Comparative Study
Stability of Boronic Esters to Hydrolysis: A Comparative Study
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DOI：
10.1246/cl.2009.750
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发表时间：
2009-07-05
影响因子：
1.6
通讯作者：
Goldoni, Luca
中科院分区：
文献类型：
--
作者：
Bernardini, Raffaella;Oliva, Ambrogio;Goldoni, Luca
硼酸酯是合成凝血酶和蛋白酶体抑制剂等生物活性化合物的关键中间体。然而，它们在合成反应期间和在生物介质中具有低水解稳定性。我们报告了几种硼酸酯的制备和它们的水解稳定性与相应的蒎烷二醇硼酸酯，这是最水解稳定的比较研究。我们发现，衍生自（1，1 ′-二环己基）-1，1 ′-二醇的硼酸酯是最稳定的。
Boronic esters are key intermediates in the synthesis of biologically active compounds such as thrombin and proteasome inhibitors. However, they have low hydrolytic stability both during synthetic reactions and in biological media. We report the preparation of several boronic esters and a comparative study of their stability to hydrolysis vs. the corresponding pinanediol boronic esters, which are among the most hydrolytically stable. We discovered that the boronic esters derived from (1,1'-bicyclohexyl)-1,1'-diol are the most stable among those examined.