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三乙基硅基醚的化学选择性脱保护

Chemoselective deprotection of triethylsilyl ethers.

作者信息

Chandra Tilak, Broderick William E, Broderick Joan B

机构信息

Department of Chemistry and Biochemistry Montana State University, Bozeman, MT 59717, USA.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2009 Nov;28(11):1016-29. doi: 10.1080/15257770903362172.

Abstract

An efficient and selective method was developed for the deprotection of triethylsilyl (TES) ethers using formic acid in methanol (5-10%) or in methylene chloride 2-5%) with excellent yields. TES ethers are selectively deprotected to the corresponding alcohols in high yields using formic acid in methanol under mild reaction conditions. Other hydroxyl protecting groups like t-butyldimethylsilyl (TBDMS) remain unaffected.

摘要

开发了一种高效且选择性的方法,用于使用甲醇(5 - 10%)或二氯甲烷(2 - 5%)中的甲酸对三乙基硅基(TES)醚进行脱保护,产率优异。在温和的反应条件下,使用甲醇中的甲酸可将TES醚选择性地高产率脱保护为相应的醇。其他羟基保护基团如叔丁基二甲基硅基(TBDMS)不受影响。

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本文引用的文献

1
Spore photoproduct lyase catalyzes specific repair of the 5R but not the 5S spore photoproduct.
J Am Chem Soc. 2009 Feb 25;131(7):2420-1. doi: 10.1021/ja807375c.
2
Vitamin B(12) and alpha-Ribonucleosides.
Tetrahedron. 2008 Jan 1;64(1):9-38. doi: 10.1016/j.tet.2007.08.061.
3
The Radical SAM Superfamily.
Crit Rev Biochem Mol Biol. 2008 Jan-Feb;43(1):63-88. doi: 10.1080/10409230701829169.
4
Thymine Photoproducts but not Thymine Dimers Found in Ultraviolet-Irradiated Bacterial Spores.
Science. 1965 Jul 16;149(3681):308-10. doi: 10.1126/science.149.3681.308.
5
Chemoselective deprotection of alpha-indole and imidazole ribonucleosides.
Nucleosides Nucleotides Nucleic Acids. 2007;26(1):1-8. doi: 10.1080/15257770601052216.
6
A new, simple, and selective palladium-catalyzed cleavage of triethylsilyl ethers.
Org Lett. 2002 Dec 26;4(26):4701-4. doi: 10.1021/ol0271382.
9
Adenosylmethionine-dependent iron-sulfur enzymes: versatile clusters in a radical new role.
J Biol Inorg Chem. 2001 Mar;6(3):209-26. doi: 10.1007/s007750100210.
10
I will survive: protecting and repairing spore DNA.
J Bacteriol. 1992 May;174(9):2737-41. doi: 10.1128/jb.174.9.2737-2741.1992.

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