Category: Protecting Groups

The TBS protecting group protects alcohols in organic synthesis, and is deprotected with fluoride anions (e.g., TBAF) or strong acids. This commonly used, bulky silyl protecting group is very resilient, allowing for selective/ orthogonal deprotection of similar groups like TMS.For silyl ethers, bigger is better!As they have 3 different mechanisms for deprotection, they’re a nice…

The Fmoc protecting group protects amines in synthesis, and is deprotected with bases such as secondary amines like piperidine. You might not expect it, but this group is very similar to other carbamate groups (e.g., Boc, Cbz) even though it is orthogonal to them. However, remember orthogonal is a relative term… But, have you heard…

The Cbz protecting group protects amines as less reactive carbamates in organic synthesis and is deprotected with hydrogenolysis. N-Cbz is orthogonal to numerous protecting groups as it’s stable to bases and acids. Its removal by reduction is unique but it has similarities to other protecting groups! You can zoom and play around with this 3D…

The Boc protecting group protects amines as less reactive carbamates in organic synthesis, and is deprotected with acid. N-Boc is a key topic during chemistry courses. Why?It nicely exemplifies important protecting group concepts and has an interesting deprotection mechanism. You can zoom and play around with this 3D model of the Boc protecting group! What…

The PMB protecting group protects alcohols as less reactive ethers in organic synthesis, and is deprotected oxidatively or with strong acids. The study of its mechanisms and properties will improve your understanding of organic chemistry concepts! You can zoom and play around with this 3D model of the PMB protecting group! What is the PMB…