82611-65-2

Basic information

• Product Name: N-CARBOBENZYLOXY-S-PHENYL-L-CYSTEINE
• Synonyms: N-CBZ-PHENYL-L-CYSTEINE;N-CBZ-S-PHENYL-L-CYSTEINE;N-BENZYLOXYCARBONYL-(S-PHENYL)-L-CYSTEINE;Z-S-PHENYL CYS-OH;CBZ-(S)-2-AMINO-3-(S-PHENYLTHIO)PROPANOIC ACID;CBZ-S-PHENYL-L-CYS-OH;CBZ-(S)-PHENYL-L-CYS;CBZ-CYS(PH)-OH
• CAS NO: 82611-65-2
• Molecular Formula: C₁₇H₁₇NO₄S
• Molecular Weight: 331.39
• EINECS: 441-530-6
• Mol File: 82611-65-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 94-97 °C(lit.)
• Boiling Point: 547.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• PKA: 3.48±0.10(Predicted)
• CAS DataBase Reference: N-CARBOBENZYLOXY-S-PHENYL-L-CYSTEINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZYLOXY-S-PHENYL-L-CYSTEINE(82611-65-2)
• EPA Substance Registry System: N-CARBOBENZYLOXY-S-PHENYL-L-CYSTEINE(82611-65-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 82611-65-2(Hazardous Substances Data)

Usage

General Description

N-Carbobenzyloxy-S-phenyl-L-cysteine is a chemical compound that is commonly used in the synthesis and modification of peptides. It is a derivative of L-cysteine, an essential amino acid, where the carboxyl group is protected by a benzyloxycarbonyl (Cbz) group. N-CARBOBENZYLOXY-S-PHENYL-L-CYSTEINE is often used as a building block for creating peptides in laboratory settings, as the Cbz group can be easily removed to reveal the free carboxylic acid group for further coupling reactions. Additionally, N-Carbobenzyloxy-S-phenyl-L-cysteine is utilized in the production of pharmaceutical drugs, as well as in the study of peptide chemistry and biology.

Upstream product

• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 108-98-5 thiophenol 
• 108-86-1 bromobenzene 
• 12775-96-1 copper 
• 67-68-5 dimethyl sulfoxide 
• 6968-11-2 N,N'-bis-benzyloxycarbonylcystine 
• 7625-65-2 L-carbobenzyloxy-β-chloroalanine 
• 132249-34-4 Methyl (S)-2-benzyloxycarbonylamino-3-methylsulfonyloxypropanoate 
• 930-69-8 sodium thiophenolate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 288588-25-0 2-benzyloxycarbonylamino-3-tert-butyldisulfanyl-propionic acid allyl ester 
• 76969-40-9 (R)-2-Benzyloxycarbonylamino-3-tert-butyldisulfanyl-propionic acid 
• 149034-35-5 Z-Cys-OAll 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 1315549-68-8 (S)-benzyl N-(chroman-3-yl)carbamate 
• 153277-22-6 (R)-benzyl (1-hydroxy-3-(phenylthio)propan-2-yl)carbamate 
• 194086-27-6 benzyl [(2R,3R)-4-chloro-3-hydroxy-1-(phenylsulfanyl)-2-butanyl]carbamate 
• 163462-16-6 benzyl [(1R)-1-[(2S)-2-oxiranyl]-2-(phenylsulfanyl)ethyl]carbamate 
• 197302-33-3 benzyl [(2R)-1-[methoxy(methyl)amino]-1-oxo-3-(phenylsulfanyl)-2-propanyl]carbamate 
• 159878-02-1 benzyl [(2R,3S)-4-chloro-3-hydroxy-1-(phenylsulfanyl)-2-butanyl]carbamate 
• 21149-17-7 methyl 2-(benzyloxycarbonylamino)acrylate 
• 153277-26-0 (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine 
• 153277-28-2 (2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine 

Relevant articles and documents

Method of making HIV protease inhibitors

A method of making HIV protease inhibitors of general formula (1): These HIV compounds inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optically other antiviral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.

Processes for producing β-halogeno-α-amino-carboxylic acids and phenylcysteine derivatives and intermediates thereof

An industrially advantageous method of producing β-halogeno-α-aminocarboxylic acids is provided. Methods are also provided of producing optically active N-protected-S-phenylcysteines having high optical purity and of intermediates thereof, respectively, in which the above production method is utilized. A method of producing β-halogeno-α-aminocarboxylic acids or salts thereof is disclosed which comprises halogenating the hydroxyl group of a β-hydroxy-α-aminocarboxylic acid (in which the basicity of the amino group in α-position is not masked by the presence of a substituent on said amino group) or a salt thereof with an acid with a halogenating agent. A method of producing optically active N-protected-S-phenylcysteines represented by the general formula (3) or salts thereof is further disclosed which comprises applying the above production method to optically active serine or a salt thereof and then carrying out treatment with an amino-protecting agent and reaction with thiophenol under a basic condition.

Method for isolation of n-protected s-phenylcysteine

This invention provides a method of isolating N-protected-S-phenylcysteine (1) of high purity, expediently, efficiently and in good yield, which comprises causing said N-protected-S-phenylcysteine to be salted out in the form of a base salt in the presence of water. wherein R1represents an amino-protecting group; R2represents a hydrogen atom or, either independently of R1or taken together with R1, represents an amino-protecting group.