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Benzyl group and derivatives: Benzyl group, benzyl radical, benzyl amine, benzyl bromide, benzyl chloroformate, and benzyl methyl ether. R = heteroatom, alkyl, aryl, allyl etc. or other substituents. In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH 2 −C 6 H 5.
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 group. The benzyl ester can be removed by hydrogenolysis, the fluorenylmethylenoxy group (Fmoc) by bases (such as piperidine), and the phenolic tert-butyl ...
Benzylamine is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis: [10] C 6 H 5 CH 2 NH 2 + 2 RBr → C 6 H 5 CH 2 NR 2 + 2 HBr C 6 H 5 CH 2 NR 2 + H 2 → C 6 H 5 CH 3 + R 2 NH. Typically a base is employed in the first step to absorb the HBr (or related acid for other kinds of ...
Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl (Cbz or Z) group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow.
A photolabile protecting group (PPG; also known as: photoremovable, photosensitive, or photocleavable protecting group) is a chemical modification to a molecule that can be removed with light. PPGs enable high degrees of chemoselectivity as they allow researchers to control spatial, temporal and concentration variables with light.
Permanent side-chain protecting groups used during Boc/benzyl SPPS are typically benzyl or benzyl-based groups. [1] Final removal of the peptide from the solid support occurs simultaneously with side chain deprotection using anhydrous hydrogen fluoride via hydrolytic cleavage. The final product is a fluoride salt which is relatively easy to ...
Bn (benzyl) Potassium hydride, tetra-n-butylammonium iodide, and benzyl bromide: Hydrogen, Pd(OH) 2 /C Secondary alcohol 2.2 was protected as the benzyl ether so that the reduction of lactone 2.3 could occur. Protection was removed much later in the synthesis to form alcohol 5.7, which was reprotected as the triethylsilyl ether.
In organic synthesis, benzyl chloride is used to introduce the benzyl protecting group in reaction with alcohols, yielding the corresponding benzyl ether, carboxylic acids, and benzyl ester. Benzoic acid (C 6 H 5 COOH) can be prepared by oxidation of benzyl chloride in the presence of alkaline KMnO 4: C 6 H 5 CH 2 Cl + 2 KOH + 2 [O] → C 6 H 5 ...