Category: Protecting Groups

  • TBS Protecting Group: TBS Protection & Deprotection

    TBS Protecting Group: TBS Protection & Deprotection

    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…

  • Fmoc Protecting Group: Fmoc Protection & Deprotection Mechanism

    Fmoc Protecting Group: Fmoc Protection & Deprotection Mechanism

    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, did you ever…

  • Cbz Protecting Group: N-Cbz Protection & Deprotection Mechanism

    Cbz Protecting Group: N-Cbz Protection & Deprotection Mechanism

    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 you should rediscover many common themes! What is the Cbz Protecting Group? Cbz is a benzyloxycarbonyl…

  • Boc Protecting Group: N-Boc Protection & Deprotection Mechanism

    Boc Protecting Group: N-Boc Protection & Deprotection Mechanism

    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. What is the Boc Protecting Group? Boc stands for tert-butyloxycarbonyl and protects amines as carbamates. More…

  • PMB Protecting Group: PMB Protection & Deprotection Mechanism

    PMB Protecting Group: PMB Protection & Deprotection Mechanism

    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 also help solidify your understanding of organic chemistry concepts! What is the PMB Protecting Group? PMB is a para-methoxybenzyl group, introduced by Yonemitsu in 1982 [1]…