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A Mild, Efficient, Inexpensive, and Selective Cleavage of Primary tert-Butyldimethylsilyl Ethers by Oxone in Aqueous Methanol

Gowravaram Sabitha, Mandali Syamala and J. S. Yadav

*Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: gowravaramsryahoo.com

G. Sabitha, M. Syamala, J. S. Yadav, Org. Lett., 1999, 1, 1701-1703.

DOI: 10.1021/ol990140h (free Supporting Information)


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Abstract

A 50% aqueous methanolic solution of Oxone selectively cleaves primary tert-butyldimethylsilyl ethers at room temperature. This method enables deprotection of TBDMS ethers of primary alcohols in the presence of TBDMS ethers of secondary and tertiary alcohols and phenols. The silyl ethers of phenols were deprotected at longer reaction times.

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Key Words

tert-butyldimethylsilyl ethers


ID: J54-Y1999