Ploypradith Poonsakdi, Cheryklin Pannarin, Niyomtham Nattisa, Bertoni Daniel R, Ruchirawat Somsak
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vipavadee-Rangsit Highway, Bangkok, Thailand 10210.
Org Lett. 2007 Jul 5;9(14):2637-40. doi: 10.1021/ol070781+. Epub 2007 Jun 12.
p-Toluene sulfonic acid (p-TsOH) immobilized either on polystyrene (PS) or silica (Si) was found to be effective in cleaving aromatic ethers containing isopropyl, tert-butyl, allyl, and benzyl groups, as well as mono-, di-, and trimethoxylated benzyl groups, in moderate to excellent yields (54-95%). These protecting groups could be selectively deprotected when they were simultaneously present on the same or different aromatic rings in a substrate.