benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate

Base Information

• Chemical Name: benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate
• CAS No.: 87053-41-6
• Molecular Formula: C₃₁H₃₉N₃O₆
• Molecular Weight: 549.667
• Mol file: 87053-41-6.mol

Synonyms:benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate

Chemical Property of benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate

There total 4 articles about benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate 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:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate (87053-41-6)

Guidance literature:

Multi-step reaction with 3 steps

1: benzotriazol-1-ol; 2,4,6-trimethyl-pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 2 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

3: benzotriazol-1-ol; 2,4,6-trimethyl-pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.6b01825

Reference yield:

L-phenylalanine benzyl ester hydrochloride (2462-32-0) → benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate (87053-41-6)

Guidance literature:

Multi-step reaction with 3 steps

1: benzotriazol-1-ol; 2,4,6-trimethyl-pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 2 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

3: benzotriazol-1-ol; 2,4,6-trimethyl-pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.6b01825

Reference yield:

(S)-tert-butyl 2-((S)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate (74257-60-6) → benzyl N-(tert-butoxycarbonyl)-L-prolyl-L-prolyl-L-phenylalaninate (87053-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

2: benzotriazol-1-ol; 2,4,6-trimethyl-pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.6b01825

upstream raw materials:

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt

N-tert-butoxycarbonyl-L-prolyl-L-proline

1-(tert-butoxycarbonyl)-L-proline

L-phenylalanine benzyl ester hydrochloride

Downstream raw materials:

Z-Arg(NO₂)-Gly-Pro-Pro-Phe-OBzl

Refernces

• 1、 Otagiri, Ken,Miyake, Ichizo,Ishibashi, Norio,Fukui, Hiroshi,Kanehisa, Hidenori,Okai, Hideo. "Studies of Bitter Peptides from Casein Hydrolyzate. II. Syntheses of Bitter Peptide Fragments and Analogs of BPIa (Arg-Gly-Pro-Pro-Phe-Ile-Val) from Casein Hydrolyzate". . p. 1116 - 1119. Retrieved 2007/10/02.