153277-33-9

Basic information

• Product Name: CBZ-S-PHENYL-L-CYSTEINE METHYL ESTER
• Synonyms: CBZ-S-PHENYL-L-CYSTEINE METHYL ESTER;N-CARBOBENZOXY-2-PHENYL-L-CYSTEINEMETHYLESTER;METHYL N-[(BENZYLOXY)CARBONYL]-S-PHENYL-L-CYSTEINATE
• CAS NO: 153277-33-9
• Molecular Formula: C₁₈H₁₉NO₄S
• Molecular Weight: 345.41
• Mol File: 153277-33-9.mol

Chemical Properties

• Boiling Point: 522.944°C at 760 mmHg
• Flash Point: 270.067°C
• Appearance: /
• Density: 1.247g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: CBZ-S-PHENYL-L-CYSTEINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: CBZ-S-PHENYL-L-CYSTEINE METHYL ESTER(153277-33-9)
• EPA Substance Registry System: CBZ-S-PHENYL-L-CYSTEINE METHYL ESTER(153277-33-9)

Safety Data

• Hazardous Substances Data: 153277-33-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CBZ-S-PHENYL-L-CYSTEINE METHYL ESTER is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique structure enables it to participate in cross-Claisen condensation reactions with alkyl acetates, leading to the formation of γ-amino β-ketoesters. These γ-amino β-ketoesters are valuable building blocks in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
In the field of organic chemistry, CBZ-S-PHENYL-L-CYSTEINE METHYL ESTER serves as a versatile reagent for the preparation of complex organic molecules. Its ability to undergo cross-Claisen condensation with alkyl acetates makes it a valuable tool for the synthesis of a wide range of compounds, including those with potential applications in various industries such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C18H19NO4S/c1-22-17(20)16(13-24-15-10-6-3-7-11-15)19-18(21)23-12-14-8-4-2-5-9-14/h2-11,16H,12-13H2,1H3,(H,19,21)/t16-/m0/s1

Upstream product

• 108-98-5 thiophenol 
• 132249-34-4 Methyl (S)-2-benzyloxycarbonylamino-3-methylsulfonyloxypropanoate 
• 108-86-1 bromobenzene 
• 12775-96-1 copper 
• 7789-45-9 copper(II)bromide 
• 3693-95-6 N-benzyloxycarbonyl cystine methyl ester 
• 1492-52-0 methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 930-69-8 sodium thiophenolate 
• 3115-68-2 tetrabutyl phosphonium bromide 
• 584-08-7 potassium carbonate 

Downstream Products

• 153277-27-1 (2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 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 
• 153277-32-8 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-methanesulfonyloxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-31-7 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-hydroxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-21-5 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane 
• 153277-34-0 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylthiopropane 
• 153379-66-9 (1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate 
• 153277-29-3 ((1S,6S,8aS)-1-Methoxymethoxy-octahydro-indolizin-6-yl)-carbamic acid benzyl ester 
• 153379-64-7 O-Deacetyl-N-(benzyloxycarbonyl)slaframine 
• 153277-22-6 (R)-benzyl (1-hydroxy-3-(phenylthio)propan-2-yl)carbamate 
• 82611-65-2 N-benzyloxycarbonyl-S-phenyl-L-cysteine 

Relevant articles and documents

Process for S-Aryl cysteine

The present invention provides methods for preparing S-aryl cysteines in enantiomeric excess of greater than about 96%. Specifically, the present invention provides enantioselective methods for preparing S-aryl cysteines starting from cystine, cysteine or

Preparation of S-aryl-cysteine and its derivatives

The present invention provides a method for preparing S-aryl cysteine. Specifically, the present invention provides enantioselective method for preparing S-aryl cysteine starting from cystine, cysteine or serine amino acid. The methods of the present inve

Process for producing of cysteine derivatives

PCT No. PCT/JP98/00101 Sec. 371 Date Apr. 22, 1999 Sec. 102(e) Date Apr. 22, 1999 PCT Filed Jan. 14, 1998 PCT Pub. No. WO98/30538 PCT Pub. Date Jul. 16, 1998This invention relates to a method comprising reacting an amino acid derivative of the following general formula (I); (wherein R1 represents an amino-protective group; R0 represents hydrogen or, taken together with R1, represents an amino-protecting group; R2 represents a carboxy-protecting group; X represents a leaving group) with a thiol compound of the following general formula (II):R3SH(II)(wherein R3 represents an alkyl group of 1 to 7 carbon atoms, an aryl group of 6 to 10 carbon atoms, or an aralkyl group of 7 to 10 carbon atoms) to give a cysteine derivative of the following general formula (III): (wherein R0, R1, R2, and R3 are as defined above), wherein the reaction is conducted in the presence of a base and water in an organic reaction solvent.

Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline

The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergoes an efficient Julia olefination with the L-serine-derived amino sulfone 29. Selective reduction of the resulting alkene 31 using diimide and cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural (-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.

A total synthesis of (-)-slaframine from (+)-cis-(2R,3S)-3-hydroxyproline

A total synthesis of the naturally occurring indolizidine (-)-Slaframine 4 has been achieved, starting from the cis-3-hydroxyproline derivative 1, in which a key step is a Julia olefination reaction using the dianion derived from the β-aminosulfone 5.