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tert-Butyloxycarbonyl protecting group. The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium hydroxide:
The Boc group can later be removed from the amine using moderately strong acids (e.g., trifluoroacetic acid). Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an ...
Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula [(CH 3) 3 COC(O)] 2 NH. It is a white solid that is soluble in organic solvents. The compound is used as a reagent for the preparation of primary amines from alkyl halides. [1] It was popularized as an alternative to the Gabriel synthesis for the same ...
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol
Piperidine is an organic compound with the molecular formula (CH 2) 5 NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH 2 –) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. [6]
β-Alanine (beta-alanine) is a naturally occurring beta amino acid, which is an amino acid in which the amino group is attached to the β-carbon (i.e. the carbon two carbon atoms away from the carboxylate group) instead of the more usual α-carbon for alanine (α-alanine). The IUPAC name for β-alanine is 3-aminopropanoic acid.
Alternatively, HBr and strong Lewis acids have been used, provided that a trap is provided for the released benzyl carbocation. [9] When the protected amine is treated by either of the above methods (i.e. by catalytic hydrogenation or acidic workup), it yields a terminal carbamic acid which then readily decarboxylates to give the free amine.
The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile amine protecting group used in organic synthesis, particularly in peptide synthesis. [1] It is popular for its stability toward acids and hydrolysis and its selective removal by weak bases, such as piperidine , without affecting most other protecting groups or sensitive ...