Farnesylcysteine methyl ester

Base Information

• Chemical Name: Farnesylcysteine methyl ester
• CAS No.: 130062-64-5
• Molecular Formula: C₁₉H₃₃NO₂S
• Molecular Weight: 339.543
• UNII: P409G2H90A
• Nikkaji Number: J1.468.817J,J587.924H
• Wikidata: Q27159423
• ChEMBL ID: CHEMBL1477730
• Mol file: 130062-64-5.mol

Synonyms:farnesylcysteine methyl ester;S-farnesylcysteine alpha-carboxyl methyl ester;S-FCME

Chemical Property of Farnesylcysteine methyl ester

Chemical Property:

• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 339.22320047
• Heavy Atom Count: 23
• Complexity: 435

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCSCC(C(=O)OC)N)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CSC[C@@H](C(=O)OC)N)/C)/C)C

Technology Process of Farnesylcysteine methyl ester

There total 1 articles about Farnesylcysteine methyl ester 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: 79.8%

Ac-Cys-OMe (7652-46-2) → methyl S-farnesylcysteine (130062-64-5)

Guidance literature:

With zinc diacetate; trifluoroacetic acid; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 20h;

DOI:10.1021/ja0119144

Reference yield: 96.0%

methyl S-farnesylcysteine (130062-64-5) + L-N-(9-(9-phenylfluorenyl))glutamic acid γ-methylester (119595-72-1) → N-[9-(9-Phenylfluorenyl)]-α-(L)-(γ-methylglutamyl)-S-farnesyl-(L)-cysteine methyl ester

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 20h;

DOI:10.1002/1521-3765(20010316)7:6<1184::AID-CHEM1184>3.0.CO;2-5

Reference yield: 94.0%

methyl S-farnesylcysteine (130062-64-5) + (S)-1-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid (170892-89-4) → (R)-2-({(S)-1-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester (170892-90-7)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

upstream raw materials:

Ac-Cys-OMe

Downstream raw materials:

(R)-2-({(S)-1-[(S)-2-(4-Acetoxy-benzyloxycarbonylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester

N^(α)-Fluorenylmethoxycarbonyl-N^(ε)-(4-tolyldiphenylmethyl)-(L)-lysyl-S-farnesyl-(L)-cysteine methyl ester

(R)-2-[2-(4-Methoxy-phenyl)-acetylamino]-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester

(R)-2-{[5-(4-Methoxy-phenyl)-furan-2-carbonyl]-amino}-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanyl)-propionic acid methyl ester