Fluorous solvent-promoted deprotection of p -methoxybenzyl- and 2,4-dimethoxyphenylmethyl-protected alcohols with camphorsulfonic acid
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ID: 318129
2026
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Abstract
Abstract We found that a catalytic amount of camphorsulfonic acid (CSA) in CF3CH2OH (TFE) deprotected p-methoxybenzyl (PMB) groups in high yield with the addition of anisole to scavenge the liberated PMB groups. This enabled selective deprotection of PMB groups even in the presence of other protecting groups such as Bn and Ac. Furthermore, by switching the acid to pyridinium p-toluenesulfonate (PPTS) and the solvent to (CF3)2CHOH (HFIP), highly chemoselective PMB deprotection was achieved even in the presence of acid-labile silyl protecting groups. The combination of PPTS and TFE proved effective for deprotection of 2,4-dimethoxyphenylmethyl groups.
| Reference Key |
openalex_W7165559442
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| Authors | Misa Matsumura, Hiroko Kawasaki, Norihiko Yamagami, Kaho IZUMI, Toshiya Yoshimizu, 片桐辰弥, Akira Nakamura, Yasuyoshi Miki, Junpei Matsuoka, Tomohiro Maegawa |
| Journal | bulletin of the chemical society of japan |
| Year | 2026 |
| DOI |
10.1093/bulcsj/uoag085
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| URL | |
| Keywords | Keywords not found |
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