Factors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acids

Kassrin TangdenpaisalSupannee SualekSomsak RuchirawatPoonsakdi PloypradithChulabhorn Research InstituteCenter for Environmental HealthThe Institute of Science and Technology for Research and Development, Mahidol University2018-09-132018-09-132009-05-30Tetrahedron. Vol.65, No.22 (2009), 4316-4325004040202-s2.0-65349143683https://repository.li.mahidol.ac.th/handle/123456789/27221Selective 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. © 2009 Elsevier Ltd. All rights reserved.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryPharmacology, Toxicology and PharmaceuticsFactors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acidsArticleSCOPUS10.1016/j.tet.2009.03.089