Tag: Protecting Groups
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Troc Protecting group Mechanism & (De)Protection
The Troc protecting group protects amines and alcohols from acid, base and electrophiles. It is deprotected by reduction. Troc (also 2,2,2-trichloroethoxycarbonyl) is a really exotic but versatile protecting group. Let’s learn why. What is the Troc Protecting Group? Troc (2,2,2-trichloroethoxycarbonyl) can convert amines or alcohols into stable carbamate or carbonate derivatives. This leads to a…
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THP Protecting Group (Tetrahydropyranyl Ether)
The THP protecting group protects alcohols as THP ethers that are stable to electrophiles, bases and other reagents. It is acid labile. THP is a much less common hydroxyl protecting group than silyl-based ones like TBS. It’s very simple but still has a unique nature and mechanism. What is the THP Protecting Group? Tetrahydropyranyl ethers…
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Acetal Protecting Group & Mechanism
The acetal protecting group protects carbonyls from bases, nucleophiles and hydride reduction. Among many variants, most common are dimethyl acetals, 1,3-dioxolanes and 1,3-dioxanes. There is no single acetal protecting group! Rather, this is a broader family of similar protecting groups. Let’s check out the properties and mechanisms of acetal protection and deprotection. What is the…
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🧠Is Organic Chemistry Hard? (Spoiler: Kinda)
“Why do they call it organic chemistry? Nothing about this feels natural.”A student, somewhere out there Organic chemistry is often perceived as one of the most challenging subjects for students. Unfortunately, this creates a lot of anxiety and misconceptions about its complexity and requirements, particularly for students in adjacent fields like medicine, pharmacy or biology.…
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Trityl Protecting Group: Trityl Chloride Protection & Deprotection
The trityl protecting group protects alcohols and amines, and can be deprotected with acids like acetic acid or TFA. The trityl group is another acid-labile protecting group that might remind you of Boc! Here we explain the “standard” trityl and exciting, more advanced versions! What is the Trityl Protecting Group? Trityl stands for triphenylmethyl, a…
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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…
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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, have you heard…
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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 it has similarities to other protecting groups! You can zoom and play around with this 3D…
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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. You can zoom and play around with this 3D model of the Boc protecting group! What…
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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 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…