(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester
• CAS No.: 22142-17-2
• Molecular Formula: C₂₄H₂₃NO₄S
• Molecular Weight: 421.517
• Mol file: 22142-17-2.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester

There total 1 articles about (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl 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: 70.0%

4-hydroxythioanisole (1073-72-9) + N-Cbz-L-Phe (1161-13-3) → (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester (22142-17-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 15h;

DOI:10.1021/jo00298a024

Reference yield: 99.0%

(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester (22142-17-2) → L-phenylalanine 4-(methylthio)phenyl ester hydrobromide (22155-47-1)

Guidance literature:

With hydrogen bromide; acetic acid; for 0.5h;

DOI:10.1021/jo00298a024

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester (22142-17-2) → (S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionic acid 4-methylsulfanyl-phenyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / 30percent HBr, AcOH / 0.5 h

2: PhCN, AcOH, DIEA / CH₂Cl₂ / 19 °C / reaction rate, half life

With hydrogen bromide; acetic acid; benzonitrile; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00298a024

upstream raw materials:

4-hydroxythioanisole

N-Cbz-L-Phe

Downstream raw materials:

L-phenylalanine 4-(methylthio)phenyl ester hydrobromide

N-tert-butyloxycarbonylglycyl-L-phenylalanine 4-(methylthio)phenylester

N-tert-butyloxycarbonylglycyl-L-phenylalanine 4-(methylsulfonyl)phenyl ester

N-tert-butyloxycarbonylglycyl-L-phenylalanyl-L-leucine p-nitroanilide