Ac-Cys(farnesyl)-OMe

Base Information

• Chemical Name: Ac-Cys(farnesyl)-OMe
• CAS No.: 135304-08-4
• Molecular Formula: C21H35 N O3 S
• Molecular Weight: 381.58
• DSSTox Substance ID: DTXSID301127191
• Nikkaji Number: J612.004K
• Mol file: 135304-08-4.mol

Synonyms:N-acetyl-S-farnesyl-L-cysteine methyl ester;N-acetyl-S-farnesylcysteine methyl ester

Chemical Property of Ac-Cys(farnesyl)-OMe

Chemical Property:

• PSA: 80.70000
• LogP: 5.20740
• Storage Temp.: -15°C
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 381.23376515
• Heavy Atom Count: 26
• Complexity: 531

Purity/Quality:

99% ^*data from raw suppliers

L-ACFM ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ac-Cys(farnesyl)-OMe

There total 2 articles about Ac-Cys(farnesyl)-OMe 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: 70.0%

Ac-Cys-OMe (7652-46-2) + farnesyl bromide (24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7) → N-acetyl-S-farnesyl-L-cysteine methyl ester (135304-08-4)

Guidance literature:

With zinc diacetate; trifluoroacetic acid; In water; N,N-dimethyl-formamide; acetonitrile; for 24h;

DOI:10.1021/ja0012016

Reference yield:

Farnesol (106-28-5) → N-acetyl-S-farnesyl-L-cysteine methyl ester (135304-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: polymer supported PPh₃; CBr₄ / CH₂Cl₂ / 5 h

2: 70 percent / zinc acetate; TFA / dimethylformamide; acetonitrile; H₂O / 24 h

With carbon tetrabromide; polymer supported PPh₃; zinc diacetate; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0012016

Reference yield: 84.0%

N-acetyl-S-farnesyl-L-cysteine methyl ester (135304-08-4) → N-acetyl-S-trans,trans-farnesyl-L-cysteine (135304-07-3)

Guidance literature:

With lithium hydroxide; In methanol; water; for 24h;

DOI:10.1021/ja0012016

upstream raw materials:

Ac-Cys-OMe

farnesyl bromide

Farnesol

Downstream raw materials:

N-acetyl-S-trans,trans-farnesyl-L-cysteine

Refernces