Ethyl L-cysteinate

Base Information

• Chemical Name: Ethyl L-cysteinate
• CAS No.: 3411-58-3
• Molecular Formula: C5H11 N O2 S
• Molecular Weight: 149.214
• Hs Code.: 2930909090
• European Community (EC) Number: 222-298-3
• UNII: CUJ92PBQ9Z
• DSSTox Substance ID: DTXSID3048364
• Nikkaji Number: J191.766H
• Wikidata: Q76000551
• ChEMBL ID: CHEMBL333513
• Mol file: 3411-58-3.mol

Synonyms:cystanin;cysteine ethyl ester;ethyl cysteine;ethyl cysteine hydrochloride;L-cysteine ethyl ester

Chemical Property of Ethyl L-cysteinate

Chemical Property:

• Vapor Pressure: 0.244mmHg at 25°C
• Melting Point: 125-127 °C
• Refractive Index: 1.49
• Boiling Point: 205.9°C at 760 mmHg
• PKA: 9.39±0.10(Predicted)
• Flash Point: 78.3°C
• PSA: 91.12000
• Density: 1.124g/cm³
• LogP: 0.50690
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 149.05104977
• Heavy Atom Count: 9
• Complexity: 97

Purity/Quality:

99% ^*data from raw suppliers

L-CYSTEINE ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CS)N
• Isomeric SMILES: CCOC(=O)[C@H](CS)N

Technology Process of Ethyl L-cysteinate

There total 15 articles about Ethyl L-cysteinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 20.0%

S-benzyl-DL-cysteine ethyl ester (953-18-4) → L-cysteine ethylester (3411-58-3,69685-04-7,85950-53-4,89830-80-8)

Guidance literature:

With titanium(III) chloride; lithium; In tetrahydrofuran; at 2.5 ℃; for 25h;

Reference yield: 7.0%

methyl 2-(4-chlorophenyl)-5,5-dimethylthiazolidine-4-carboxylate (1174759-04-6) + (2RS,4R)-2-phenylthiazolidine-4-carboxylic acid ethyl ester (189228-43-1) → L-cystein ethyl ester (3411-58-3) + methyl 5,5-dimethyl-2-phenylthiazolidine-4-carboxylate (155346-60-4) + (4R)-ethyl-2-(4-chlorophenyl) thiazolidine-4-carboxylate (78979-47-2)

Guidance literature:

In methanol; at 20 ℃; for 48h; pH=4; aq. acetate buffer;

DOI:10.1021/ol901104a

Reference yield: 7.0%

4-methyl-benzaldehyde (104-87-0) + 4-chlorobenzaldehyde (104-88-1) + 4-methoxy-benzaldehyde (123-11-5) + (2RS,4R)-2-phenylthiazolidine-4-carboxylic acid ethyl ester (189228-43-1) + m-tolyl aldehyde (620-23-5) → L-cystein ethyl ester (3411-58-3) + (4R) ethyl 2-(3-methylphenyl)thiazolidine-4-carboxylate (1174759-03-5) + (4R)-ethyl-2-(4-chlorophenyl) thiazolidine-4-carboxylate (78979-47-2) + (4R) ethyl 2-(4-methoxyphenyl)thiazolidine-4-carboxylate (78979-46-1) + (4R) ethyl 2-(4-methylphenyl)thiazolidine-4-carboxylate (368427-19-4)

Guidance literature:

In methanol; at 20 ℃; for 144h; pH=4; aq. acetate buffer;

DOI:10.1021/ol901104a

upstream raw materials:

ethanol

DL-cysteine hydrochloride

S-benzyl-DL-cysteine ethyl ester

ethyl cysteinate hydrochloride

Downstream raw materials:

Cystein-hydrazid

5-thio-2-nitrobenzoic acid

9,10-phenanthrenequinone

2-Amino-3-(10-oxo-9,10-dihydro-anthracen-9-ylsulfanyl)-propionic acid ethyl ester

Refernces

Total synthesis of the latrunculins

10.1021/ja00034a036

The research details the total synthesis of latrunculins A and B, two architecturally novel toxins isolated from the Red Sea sponge Latrunculia magnifica. The study presents highly convergent and stereocontrolled routes to achieve these syntheses, with the longest linear sequences being 16 and 12 steps, respectively. Key chemicals and strategies involved in the synthesis include the aldol reaction of aldehyde (-)-12 with methyl ketone (-)-13, an acid-catalyzed reorganization-equilibration of ortho ester (-)-11, and a Mitsunobu macrolide cyclization. The synthesis also involves the preparation of various intermediates such as aldehyde (-)-12 derived from (f)-2-allylcyclopentanone and (+)-(R,R)-2,3-butanediol, and ketone (-)-13 derived from L-cysteine ethyl ester. The research highlights the challenges and solutions in achieving the correct stereochemistry and configuration of the target compounds, showcasing the importance of protecting group strategies and selective reagents like lithium bis(trimethylsilyl)amide and dibutylboron triflate. The successful synthesis of latrunculins A and B provides valuable insights into the structure and function of these toxins, which have significant biological profiles and potential applications in studying actin microfilament structure and function.

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