N-palmitoylcysteine alpha-methyl ester

Base Information

• Chemical Name: N-palmitoylcysteine alpha-methyl ester
• CAS No.: 73793-95-0
• Molecular Formula: C₂₀H₃₉NO₃S
• Molecular Weight: 373.601
• Mol file: 73793-95-0.mol

Synonyms:methyl n-hexadecanoyl-l-cysteinate;L-Cysteine,N-(1-oxohexadecyl)-,methyl ester;

Chemical Property of N-palmitoylcysteine alpha-methyl ester

Chemical Property:

• Vapor Pressure: 3.63E-10mmHg at 25°C
• Boiling Point: 500.9°Cat760mmHg
• PKA: 9.17±0.10(Predicted)
• Flash Point: 256.8°C
• PSA: 97.69000
• Density: 0.976g/cm³
• LogP: 5.89560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-palmitoylcysteine alpha-methyl ester

There total 3 articles about N-palmitoylcysteine alpha-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: 81.0%

Ν,Ν'-bis(hexadecanoyl)-L-cystine dimethyl ester (73793-92-7) → Nα-Hexadecanoyl-L-cysteine methyl ester (73793-95-0)

Guidance literature:

With 1,4-dithio-erythritol; triethylamine; In chloroform; for 48h;

Reference yield:

L-cysteine methyl ester hydrochloride (18598-63-5) + rac.-3-hexadecanoyl-4-methoxycarbonyl-1,3-thiazolidine-2-thione (81912-43-8) → Nα-Hexadecanoyl-L-cysteine methyl ester (73793-95-0)

Guidance literature:

With triethylamine; In dichloromethane; for 1.5h;

DOI:10.1016/S0040-4039(00)86786-6

Reference yield:

n-hexadecanoyl chloride (112-67-4) → Nα-Hexadecanoyl-L-cysteine methyl ester (73793-95-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / N-methylmorpholine / CHCl₃ / 2 h / Ambient temperature

2: 81 percent / triethylamine, 1,4-dithioerythritol / CHCl₃ / 48 h

With 4-methyl-morpholine; 1,4-dithio-erythritol; triethylamine; In chloroform;

upstream raw materials:

L-cysteine methyl ester hydrochloride

rac.-3-hexadecanoyl-4-methoxycarbonyl-1,3-thiazolidine-2-thione

Ν,Ν'-bis(hexadecanoyl)-L-cystine dimethyl ester

n-hexadecanoyl chloride

Downstream raw materials:

N-Hexadecanoyl-S-<(2R,S)-2,3-dihexadecanoyloxypropyl>-(R)-cysteine methyl ester

Refernces

• 1、 Nagao, Yoshimitsu,Yagi, Masahiro,Ikeda, Takao,Fujita, Eiichi. "A NEW DETERMINATION OF THE ABSOLUTE CONFIGURATION OF THE CHIRAL AMINE". . p. 205 - 208. Retrieved 2007/10/02.