Octet / Collection
Protecting Groups
What each group protects, how it goes on and how it comes off.
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All Protecting Groups
What each group protects, how it goes on and how it comes off.
tert-Butyldimethylsilyl
tert-Butyldimethylsilyl (TBS or TBDMS) protects alcohols. Install with TBSCl, imidazole, DMF. Remove with TBAF (tetrabutylammonium fluoride) or HF. Very common. Stable to many conditions. Removed by fluoride.
Benzyl
Benzyl (Bn) protects alcohols, carboxylic acids. Install with BnBr, NaH (for alcohols). Remove with H₂/Pd (hydrogenolysis). Stable to base and mild acid. Removed under hydrogenation.
Acetyl
Acetyl (Ac) protects alcohols, amines. Install with Ac₂O or AcCl, pyridine. Remove with NaOH/MeOH or K₂CO₃/MeOH. Forms ester (for OH) or amide (for NH₂). Removed by base hydrolysis.
Acetal
Acetal (-) protects aldehydes, ketones. Install with Diol (ethylene glycol), acid catalyst, remove H₂O. Remove with Aqueous acid (H₃O⁺). Stable to base, nucleophiles, reducing agents. Removed by acid.
tert-Butoxycarbonyl
tert-Butoxycarbonyl (Boc) protects amines. Install with Boc₂O, base. Remove with TFA (trifluoroacetic acid) or HCl. Common in peptide synthesis. Orthogonal to Fmoc.
Fluorenylmethyloxycarbonyl
Fluorenylmethyloxycarbonyl (Fmoc) protects amines. Install with Fmoc-Cl, base. Remove with Piperidine (base). Removed by base (not acid). Orthogonal to Boc. Standard in solid-phase peptide synthesis.
Methyl ester
Methyl ester (-) protects carboxylic acids. Install with MeOH, H₂SO₄ (Fischer) or CH₂N₂. Remove with NaOH/H₂O (saponification) or LiOH. Simple protection. Easily hydrolyzed back to acid.
Tetrahydropyranyl
Tetrahydropyranyl (THP) protects alcohols. Install with DHP (dihydropyran), PPTS (acid). Remove with Aqueous acid or PPTS/MeOH. Creates acetal. Stable to base. Introduces chirality (diastereomers).
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