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Benzyl chloroformate is commonly used in organic synthesis for the introduction of the benzyloxycarbonyl (formerly called carboxybenzyl) protecting group for amines.The protecting group is abbreviated Cbz or Z (in honor of discoverer Zervas), hence the alternative shorthand designation for benzyl chloroformate as Cbz-Cl or Z-Cl.
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 group.
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Benzyl carbamate is the organic compound with the formula C 6 H 5 CH 2 OC(O)NH 2. The compound can be viewed as the ester of carbamic acid (O=C(OH)(NH 2)) and benzyl alcohol, although it is produced from benzyl chloroformate with ammonia. [1] It is a white solid that is soluble in organic solvents and moderately soluble in water.
The carbamate is formed when an uncharged lysine side chain near the ion reacts with a carbon dioxide molecule from the air (not the substrate carbon dioxide molecule), which then renders it charged, and, therefore, able to bind the Mg 2+ ion. [11] Carbamate formation is a critical step in the formation of biomass from atmospheric carbon dioxide.
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For example, benzyl chloroformate is used to introduce the Cbz (carboxybenzyl) protecting group and fluorenylmethyloxycarbonyl chloride is used to introduce the FMOC protecting group. Chloroformates are popular in the field of chromatography as derivatization agents.