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How to describe removal of protecting groups

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In synthetic chemistry, protecting groups (also sometimes referred to as protective groups) are used to mask reactive functional groups, either to prevent them from being transformed by a given set of reaction conditions or to prevent them from interfering with a desired reaction.

Functional groups are usually described as being protected or deprotected, and protecting groups can be described as being installed, added, or put on and then as being removed or cleaved. (Note that these are not the only options.) Here are some typical examples of standard usage:

  • Strategies involving protection and deprotection of the alcohol introduce at least two extra steps into the synthetic sequence.
  • The hydroxyl group at the 4-position was protected with an acetate group.
  • The aldehyde was protected as a dimethyl acetal so that the ester could be reduced to the corresponding primary alcohol.
  • The phenolic tert-butyldimethylsilyl ether was cleaved in methanol under mild conditions.
  • The reaction gave a moderate yield of the two isomers, which could not be separated until the ketal protecting group was removed.
  • The benzyl protecting group was removed by catalytic hydrogenation over Raney nickel.

However, I often run across sentences such as the following:

  • This is a promising method for chemoselective deprotection of acetal protecting groups.
  • The alkyl tert-butyldimethylsilyl ether was deprotected by means of a heterogeneous reaction catalyzed by silver-exchanged silicotungstic acid.
  • We selectively deprotected the N-Boc group by using bismuth(III) trichloride in acetonitrile/water.

These sentences imply that it was the protecting group—an acetal, a tert-butyldimethylsilyl ether, or an N-Boc group, respectively—that was protected and must be deprotected. However, what was in fact protected was the masked functional group—an aldehyde, a hydroxyl group, or an amine, respectively,. This problem is easy to fix. You can revise either to

  • This is a promising method for chemoselective removal deprotection of acetal protecting groups.
  • The alkyl tert-butyldimethylsilyl ether was cleaved deprotected by means of a heterogeneous reaction catalyzed by silver-exchanged silicotungstic acid.
  • We selectively removed deprotected the N-Boc group by using bismuth(III) trichloride in acetonitrile/water.

or to something like

  • This is a promising method for chemoselective deprotection of aldehydes acetal protecting groups.
  • The hydroxyl group alkyl tert-butyldimethylsilyl ether was deprotected by means of a heterogeneous reaction catalyzed by silver-exchanged silicotungstic acid.
  • We selectively deprotected the amine N-Boc group by using bismuth(III) trichloride in acetonitrile/water.

The best choice will depend on the context.


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