引用本文:
Jian Rong Zhu, Ji Jun Xue, Wen Ze Li, Xue Song Chen, Ying Li. Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases[J]. Chinese Chemical Letters,
2010, 21(3): 273-276.
doi:
10.1016/j.cclet.2009.11.049
Citation: Jian Rong Zhu, Ji Jun Xue, Wen Ze Li, Xue Song Chen, Ying Li. Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases[J]. Chinese Chemical Letters, 2010, 21(3): 273-276. doi: 10.1016/j.cclet.2009.11.049
Citation: Jian Rong Zhu, Ji Jun Xue, Wen Ze Li, Xue Song Chen, Ying Li. Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases[J]. Chinese Chemical Letters, 2010, 21(3): 273-276. doi: 10.1016/j.cclet.2009.11.049
Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases
摘要:
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.
English
Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases
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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