Mild and Selective Deprotection of tert-Butyl(dimethyl)silyl Ethers with Catalytic Amounts of Sodium Tetrachloroaurate(III) Dihydrate

被引：12
|
作者：
Zhang, Qi [1 ]
Kang, Xiuqin [1 ]
Long, Lei [1 ]
Zhu, Lijuan [1 ]
Chai, Yonghai [2 ]
机构：
[1] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710062, Peoples R China
[2] Shaanxi Normal Univ, Key Lab Appl Surface & Colloid Chem, MOE, Xian 710062, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 01期
基金：
中国国家自然科学基金; 高等学校博士学科点专项科研基金;
关键词：
deprotection; silyl ethers; alcohols; ethers; catalysis; gold; TERT-BUTYLDIMETHYLSILYL ETHERS; SILYL PROTECTING GROUPS; CHEMOSELECTIVE DEPROTECTION; EFFICIENT METHOD; TBDMS ETHERS; OXIDATIVE DEPROTECTION; REDUCTIVE CLEAVAGE; FACILE; ALCOHOLS; TBS;
D O I：
10.1055/s-0034-1379032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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收藏
页码：55 / 64
页数：10
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