高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 316.

• Organic Synthesis Chemistry • 上一篇    下一篇

A Novel Desilylating Method for tert-Butyldimethylsilyl,tert-Butyldiphenylsilyl and Triisopropylsilyl Ethers

Adam Shih-Yuan Lee, Jiun-Jie Shie, Hsiu-Chih Yeh   

  1. Department of Chemistry, Tamkang University, Tamsui, Taiwan, 251
  • 出版日期:1998-12-31 发布日期:1998-12-31

A Novel Desilylating Method for tert-Butyldimethylsilyl,tert-Butyldiphenylsilyl and Triisopropylsilyl Ethers

Adam Shih-Yuan Lee, Jiun-Jie Shie, Hsiu-Chih Yeh   

  1. Department of Chemistry, Tamkang University, Tamsui, Taiwan, 251
  • Online:1998-12-31 Published:1998-12-31

摘要: In order to synthesize complicated medicinal compounds, chemists have developed increasingly satisfactory protective groups and effective methods for the formation and cleavage of protected compounds. The selective method to remove protective groups is an important tool in organic synthesis. Transformation of an alcohol to its corresponding silyl ether is a common and useful method for protecting hydroxyl groups. Within the silyl ethers,tert-butyldimethylsilyl,tert-butyldiphenylsilyl and triisopropylsilyl ethers are the most commonly used protecting groups. The cleavage of the Si-O bonds of these silyl ethers is typically performed with fluoride ion or under harsh acidic or basic conditions. Herewith, we wish to report a highly efficient and mildly acidic desilylating method for tert-butyldimethylsilyl,tert-butyldiphenylsilyl and triisopropylsilyl ethers.

Abstract: In order to synthesize complicated medicinal compounds, chemists have developed increasingly satisfactory protective groups and effective methods for the formation and cleavage of protected compounds. The selective method to remove protective groups is an important tool in organic synthesis. Transformation of an alcohol to its corresponding silyl ether is a common and useful method for protecting hydroxyl groups. Within the silyl ethers,tert-butyldimethylsilyl,tert-butyldiphenylsilyl and triisopropylsilyl ethers are the most commonly used protecting groups. The cleavage of the Si-O bonds of these silyl ethers is typically performed with fluoride ion or under harsh acidic or basic conditions. Herewith, we wish to report a highly efficient and mildly acidic desilylating method for tert-butyldimethylsilyl,tert-butyldiphenylsilyl and triisopropylsilyl ethers.

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