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ChemInform Abstract: A Simple and Highly Chemoselective Desilylation of tert- Butyldimethylsilyl Ethers.

โœ Scribed by A. S.-Y. LEE; H.-C. YEH; M.-H. TSAI


Book ID
112024657
Publisher
John Wiley and Sons
Year
2010
Weight
26 KB
Volume
27
Category
Article
ISSN
0931-7597

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A modified literature procedure is presented for desilylating primary and secondary tert-butyldimethylsilyl ethers involving TMSOTf followed by breakdown of the b/s-silyloxonium ion in methanol. The chemoselectivity of the process with respect to TBDPS, TIPS, MEM, ester, ketal, acetate, benzoate and

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Desilylation of t-Butyldimethylsilyl Ethers of Hydroxyquinones. -The most general of three applied different desilylating procedures is the cleavage of the O-Si bond with Bu 4 NF. The other two methods use KF as desilylating agent in either the presence of a catalytic amount HBr, or basic Al 2 O 3 .