Issue 12, 2008
From the journal:

Organic & Biomolecular Chemistry

The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide†

Syed Tasadaque A. Shaha  and  Patrick J. Guiry*a  

* Corresponding authors

a Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland
E-mail: patrick.guiry@ucd.ie
Fax: +353 1 716 2501

Abstract

An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities of TMSBr.

Graphical abstract: The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide

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Article information

DOI
https://doi.org/10.1039/B803949F
Article type
Paper
Submitted
07 Mar 2008
Accepted
10 Mar 2008
First published
18 Apr 2008

Org. Biomol. Chem., 2008,6, 2168-2172

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The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide

S. T. A. Shah and P. J. Guiry, Org. Biomol. Chem., 2008, 6, 2168 DOI: 10.1039/B803949F

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