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

Issued Date

2009-05-30

Resource Type

Article

ISSN

00404020

DOI

10.1016/j.tet.2009.03.089

Other identifier(s)

2-s2.0-65349143683

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron. Vol.65, No.22 (2009), 4316-4325

Suggested Citation

Kassrin Tangdenpaisal, Supannee Sualek, Somsak Ruchirawat, Poonsakdi Ploypradith Factors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acids. Tetrahedron. Vol.65, No.22 (2009), 4316-4325. doi:10.1016/j.tet.2009.03.089 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/27221

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Title

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

Author(s)

Kassrin Tangdenpaisal
 Supannee Sualek
 Somsak Ruchirawat
 Poonsakdi Ploypradith

Other Contributor(s)

Chulabhorn Research Institute
 Center for Environmental Health
 The Institute of Science and Technology for Research and Development, Mahidol University

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. © 2009 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

Availability

URI

https://repository.li.mahidol.ac.th/handle/123456789/27221

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Scopus 2006-2010