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Debenzylation/ketal removal

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30 September 2008

Protecting group removal can be the source of significant challenges, especially when other sensitive groups are present in the molecule. S Py et al (Org. Lett., 2008, 10 (14), 2967-2970) report a procedure for cleavage of benzyl ethers in the presence of hydrogenation-sensitive nitrone and N-hydroxypyrrolidine functionality and dimethyl ketal where the typical acidic conditions can be compromised by other side reactions. The group established that boron trichloride in DCM at 0°C was extremely effective. Example deprotections are given in the scheme.

Overall, the use of the Lewis acid boron trichloride promotes an efficient cleavage of benzyl ethers and dimethyl ketals.