Phenylalanylphenylalanine methyl ester

Base Information

• Chemical Name: Phenylalanylphenylalanine methyl ester
• CAS No.: 13082-29-6
• Molecular Formula: C₁₉H₂₂N₂O₃
• Molecular Weight: 326.395
• DSSTox Substance ID: DTXSID50926928
• Nikkaji Number: J558.283K
• Wikidata: Q82901536
• Mol file: 13082-29-6.mol

Synonyms:Phe-Phe-OMe;phenylalanylphenylalanine methyl ester;phenylalanylphenylalanine methyl ester hydrobromide;phenylalanylphenylalanine methyl ester hydrochloride

Chemical Property of Phenylalanylphenylalanine methyl ester

Chemical Property:

• Vapor Pressure: 1.79E-11mmHg at 25°C
• Boiling Point: 533.8°C at 760 mmHg
• PKA: 13.71±0.46(Predicted)
• Flash Point: 276.6°C
• PSA: 81.42000
• Density: 1.168g/cm³
• LogP: 2.54810
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 326.16304257
• Heavy Atom Count: 24
• Complexity: 401

Purity/Quality:

2-(2-Amino-3-phenylpropionylamino)-3-phenylpropionic acid methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC2=CC=CC=C2)N
• Isomeric SMILES: COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC2=CC=CC=C2)N

Technology Process of Phenylalanylphenylalanine methyl ester

There total 24 articles about Phenylalanylphenylalanine 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: 99.0%

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate (13122-89-9) → L-phenylalanyl-L-phenylalanine methyl ester (13082-29-6,80546-83-4,94788-14-4,120706-60-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2.25h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00036

Reference yield: 73.0%

N-(benzyloxycarbonyl)-L-phenylalanyl-L-phenylalanine methyl ester (4892-10-8) → L-phenylalanyl-L-phenylalanine methyl ester (13082-29-6,80546-83-4,94788-14-4,120706-60-7)

Guidance literature:

With formic acid; palladium; In methanol; at 20 ℃; for 4h;

Reference yield: 68.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → L-phenylalanyl-L-phenylalanine methyl ester (13082-29-6,80546-83-4,94788-14-4,120706-60-7)

Guidance literature:

L-phenylalanine; With phosphoric acid; In water; acetonitrile;

With methyloxirane; In dimethyl sulfoxide; at 40 ℃;

methyl (2S)-2-amino-3-phenylpropanoate; Further stages;

DOI:10.1080/10426507.2010.501319

upstream raw materials:

N-(benzyloxycarbonyl)-L-phenylalanyl-L-phenylalanine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate

L-phenylalanine allyl ester p-toluenesulfonic acid salt

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate

Downstream raw materials:

cinnamoyl-Phe-Phe-H

C₂₂H₂₄N₂O₄

Refernces

• 1、 Dolai, Gobinda,Giri, Rajat Subhra,Roy, Sayanta,Mandal, Bhubaneswar. "Crystal structure and supramolecular arrangement of heterochiral tripeptides". . . Retrieved 2021/04/15.
• 2、 Cindro, Nikola,Horvat, Gordan,Rinkovec, Tamara,Riva, Davide,Speranza, Giovanna,Tomi?i?, Vladislav,Vidovi?, Nikolina. "Chloride-Assisted Peptide Macrocyclization". supporting information. . Retrieved 2020/03/26.