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Factors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acids |
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| Authors: | Kassrin Tangdenpaisal Somsak Ruchirawat Poonsakdi Ploypradith |
| Affiliation: | a Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vipavadee-Rangsit Highway, Bangkok 10210, Thailand b Program in Chemical Biology, Chulabhorn Graduate Institute and the Center of Excellence on Environmental Health, Toxicology and Management of Chemicals, Vipavadee-Rangsit Highway, Bangkok 10210, Thailand c Program on Research and Development of Synthetic Drugs, Institute of Science and Technology for Research and Development, Mahidol University, Salaya Campus, Nakhon Pathom, Thailand |
| Abstract: | Selective deprotection of aromatic ethers bearing two protecting groups on the same aromatic ring by solid-supported acids (Amberlyst-15 and PTS-Si) was systematically investigated. ortho-Directing protonation by the carbonyl group as well as carbocation stability and quenching are the important determining factors for the orthogonal deprotection process. Stablilized carbocations (e.g., those from the MOM and PMB groups) could be removed with high selectivity. |
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