使用三氟甲磺酸三烷基硅酯和2,2'-联吡啶对芳基甲氧基甲基醚进行化学选择性转化

Yanagihara Mizushi, Ohta Reiya, Murai Kenichi, Arisawa Mitsuhiro, Fujioka Hiromichi

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.

ACS Omega. 2019 May 14;4(5):8465-8471. doi: 10.1021/acsomega.9b00643. eCollection 2019 May 31.

Aromatic methoxymethyl (MOM) ethers behave differently from aliphatic MOM ethers upon treatment with trialkylsilyl triflate (RSiOTf) and 2,2'-bipyridyl. The aromatic MOM ethers are first converted to silyl ethers and subsequently deprotected by hydrolysis to give the mother alcohols when the RSiOTf used is trimethylsilyl triflate (TMSOTf). Conversely, direct conversion of aromatic MOM ethers to aromatic triethylsilyl (TES) ethers is possible when the RSiOTf used is triethylsilyl triflate (TESOTf).

在用三烷基甲硅烷基三氟甲磺酸盐（RSiOTf）和2,2'-联吡啶处理时，芳族甲氧基甲基（MOM）醚的行为与脂肪族MOM醚不同。当使用的RSiOTf是三甲基甲硅烷基三氟甲磺酸盐（TMSOTf）时，芳族MOM醚首先转化为甲硅烷基醚，随后通过水解脱保护得到母体醇。相反，当使用的RSiOTf是三乙基甲硅烷基三氟甲磺酸盐（TESOTf）时，芳族MOM醚可以直接转化为芳族三乙基甲硅烷基（TES）醚。