The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Concise Asymmetric Syntheses of Radicicol and Monocillin I》. Authors are Garbaccio, Robert M.; Stachel, Shawn J.; Baeschlin, Daniel K.; Danishefsky, Samuel J..The article about the compound:(S)-Methyl 3-hydroxybutanoatecas:53562-86-0,SMILESS:C[C@H](O)CC(OC)=O).Safety of (S)-Methyl 3-hydroxybutanoate. Through the article, more information about this compound (cas:53562-86-0) is conveyed.
Radicicol (I) exhibits potent anticancer properties in vitro, which are likely to be mediated through its high affinity (20 nM) for the mol. chaperone Hsp90. Recently, we reported the results of a synthetic program targeting I and monocillin I (II), highlighted by the application of ring-closing metathesis to macrolide formation. These efforts resulted in a highly convergent synthesis of radicicol di-Me ether but failed in the removal of the two aryl Me ethers. Simple exchange of these Me ethers with more labile functionalities disabled a key esterification in the initial route. Through extended experimentation, a successful route to both natural products was secured, along with some intriguing results that emphasize the implications of this design on a broad range of fused benzoaliph. targets, including analogs of these natural products.
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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics