N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl ester

Base Information

• Chemical Name: N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl ester
• CAS No.: 179869-83-1
• Molecular Formula: C₄₂H₇₃NO₆
• Molecular Weight: 688.045
• Mol file: 179869-83-1.mol

Synonyms:

Chemical Property of N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl ester

There total 8 articles about N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl 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:

13-methyltetradecanoic acid (2485-71-4) → N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl ester (179869-83-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / DCC, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

2: 90 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / Ambient temperature

3: oxalyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

With dmap; oxalyl dichloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(98)83044-5

Reference yield:

(R)-15-Methyl-3-(13-methyl-tetradecanoyloxy)-hexadecanoic acid benzhydryl ester (179869-82-0) → N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl ester (179869-83-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / Ambient temperature

2: oxalyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

With oxalyl dichloride; hydrogen; triethylamine; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(98)83044-5

Reference yield:

(R)-3-Hydroxy-15-methyl-hexadecanoic acid benzhydryl ester (179869-81-9) → N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-serine benzyl ester (179869-83-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / DCC, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

2: 90 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / Ambient temperature

3: oxalyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

With dmap; oxalyl dichloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(98)83044-5

upstream raw materials:

L-serine benzyl ester

(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acid

L-serine benzyl ester hydrochloride

13-methyltetradecanoic acid

Downstream raw materials:

N-{N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]-L-seryl}glycine benzyl ester

Refernces

• 1、 Shiozaki, Masao,Deguchi, Noriko,Mochizuki, Takashi,Nishijima, Masahiro. "Stereocontrolled synthesis of all stereoisomers of the proposed flavolipin". . p. 3875 - 3876. Retrieved 2007/10/03.