Carbobenzyloxyprolylvaline benzyl ester

Base Information

• Chemical Name: Carbobenzyloxyprolylvaline benzyl ester
• CAS No.: 99909-22-5
• Molecular Formula: C₂₅H₃₀N₂O₅
• Molecular Weight: 438.524
• European Community (EC) Number: 667-880-1
• Mol file: 99909-22-5.mol

Synonyms:AKOS024432596;CARBOBENZYLOXYPROLYLVALINE BENZYL ESTER

Chemical Property of Carbobenzyloxyprolylvaline benzyl ester

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 438.21547206
• Heavy Atom Count: 32
• Complexity: 626

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)OCC1=CC=CC=C1)NC(=O)C2CCCN2C(=O)OCC3=CC=CC=C3

Technology Process of Carbobenzyloxyprolylvaline benzyl ester

There total 2 articles about Carbobenzyloxyprolylvaline 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: 80.0%

L-valine benzyl ester p-toluenesulfonate salt (16652-76-9) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-Pro-Val-OBzl (99909-22-5)

Guidance literature:

With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; N,N-dimethyl-formamide; 1 h on ice bath, then room temperature;

Reference yield: 59.0%

L-valine benzyl ester (21760-98-5) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-Pro-Val-OBzl (99909-22-5)

Guidance literature:

N-Benzyloxycarbonyl-L-proline; With bis(2-chlorophenyl)borinic acid; In fluorobenzene; at 65 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

L-valine benzyl ester; In fluorobenzene; at 65 ℃; for 48h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c5cc06177f

Reference yield: 78.0%

Z-Pro-Val-OBzl (99909-22-5) → (2S)-2-[({(2S)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrol-2-yl}carbonyl)amino]-3-methylbutanoic acid (21285-27-8)

Guidance literature:

With sodium hydroxide; In methanol; for 1h; Ambient temperature;

upstream raw materials:

L-valine benzyl ester p-toluenesulfonate salt

N-Benzyloxycarbonyl-L-proline

L-valine benzyl ester

Downstream raw materials:

(2S)-2-[({(2S)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrol-2-yl}carbonyl)amino]-3-methylbutanoic acid

Z-Pro-Val-Leu-Gly-OH

Z-Pro-Val-Leu-Gly-OBzl

Z-Pro-Val-Leu-Gly-Pro-Val-O-Bzl

Refernces

• 1、 Shinoda, Ichizo,Fushimi, Akira,Kato, Hironobu,Okai, Hideo,Fukui, Sazuko. "Bitter Taste of Synthetic C-Terminal Tetrapeptide of Bovine β-Casein, H-Pro196-Val-Leu-Gly-Pro-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val209-OH, and Its Related Peptides". . p. 2587 - 2596. Retrieved 2007/10/02.