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Mild and Selective Deprotection of tert-Butyl(dimethyl)silyl Ethers with Catalytic­ Amounts of Sodium Tetrachloroaurate(III) Dihydrate
Synthesis ( IF 2.2 ) Pub Date : 2014-09-15 , DOI: 10.1055/s-0034-1379032
Qi Zhang 1 , Yonghai Chai 2 , Xiuqin Kang 1 , Lei Long 1 , Lijuan Zhu 1
Affiliation  

Abstract

A simple and mild method for the removal of tert-butyl(dimethyl)silyl (TBS) protecting groups with catalytic amounts of sodium tetrachloroaurate(III) dihydrate is described. The procedure permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher reaction temperature.

A simple and mild method for the removal of tert-butyl(dimethyl)silyl (TBS) protecting groups with catalytic amounts of sodium tetrachloroaurate(III) dihydrate is described. The procedure permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher reaction temperature.



中文翻译:

催化量的二水合四氯金酸钠(III)对叔丁基(二甲基)甲硅烷基醚进行温和选择性脱保护

摘要

描述了一种简单温和的方法,该方法用催化量的二水合四氯金酸钠(III)二水合物除去丁基(二甲基)甲硅烷基(TBS)保护基。该方法允许在芳族TBS醚,脂族三异丙基甲硅烷基醚,脂族叔丁基(二苯基)甲硅烷基醚或空间受阻的脂族TBS醚的存在下,以良好的产率至优异的产率对脂族TBS醚进行选择性脱保护。另外,通过使用较大量的催化剂和较高的反应温度,也可以在一锅中将TBS醚转化为4-甲氧基苄基醚或甲基醚。

描述了一种简单温和的方法,该方法用催化量的二水合四氯金酸钠(III)二水合物除去丁基(二甲基)甲硅烷基(TBS)保护基。该方法允许在芳族TBS醚,脂族三异丙基甲硅烷基醚,脂族叔丁基(二苯基)甲硅烷基醚或空间受阻的脂族TBS醚的存在下,以良好的产率至优异的产率对脂族TBS醚进行选择性脱保护。另外,通过使用较大量的催化剂和较高的反应温度,也可以在一锅中将TBS醚转化为4-甲氧基苄基醚或甲基醚。

更新日期:2014-09-15
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