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| Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases |
| Jian Rong Zhua, Ji Jun Xuea, Wen Ze Lib, Xue Song Chena, Ying Lia |
a The State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
b Zhejiang Jiuzhou Pharmaceutical Co. Ltd., 99 Waisha Rd., Jiaojiang Taizhou City, Zhejiang 318000, China |
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Abstract Simple organic nitrogen bases, such as Et3N, pyridine, DBU, etc., were found to be convenient and useful reagents for deprotection of TBDMS groups on acidic hydroxyl groups. The efficiency of these bases has an apparent order: 1°amine > 2°amine > 3°amine and aliphatic base>aromatic base. In aqueous DMSO and at room temperature, phenolic TBDMS ethers were removed selectively in the presence of alcoholic TBDMS ethers. And catalytic base can make these reactions complete. This method is high-yielding, fast, clean, safe and cost-effective.
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Received: 15 June 2009
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| Fund:We are grateful to Dr. Qiang Gao (Shanghai Haoyuan Express Chemical Company Ltd. Of China) for his donation of actin and their helpful advice and discussions. Project No. 20672050 supported by the National Natural Science Foundation of China. |
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Corresponding Authors:
Ji Jun Xue,E-mail addresses:xuejj@lzu.edu.cn;Ying Li,E-mail addresses:liying@lzu.edu.cn
E-mail: xuejj@lzu.edu.cn;liying@lzu.edu.cn
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