Effective chemoselective deprotection of 3,4-dimethoxybenzyl (DMB) ethers in the presence of benzyl and p-methoxybenzyl (PMB) ethers by phenyliodine(III) bis(trifluoroacetate) (PIFA) |
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| Authors: | Kazuhiro WatanabeTadashi Katoh |
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| Institution: | Laboratory of Synthetic and Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan |
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| Abstract: | In this Letter, a selective deprotection of the alcohol protecting 3,4-dimethoxybenzyl (3,4DMB) group is described. The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) is found to be an efficient reagent for the chemoselective deprotection of 3,4DMB ethers in the presence of benzyl, p-methoxybenzyl, methoxymethyl, tert-butyldimethylsilyl, and tert-butyldiphenylsilyl ethers under mild conditions. This is the first example of the selective deprotection of the 3,4DMB group from a hydroxy group with PIFA. |
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| Keywords: | Phenyliodine(III) bis(trifluoroacetate) (PIFA) 3 4-Dimethoxybenzyl (3 4DMB) p-Methoxybenzyl (PMB) Selective deprotection Charge transfer (CT) complex |
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