Phebestin

Base Information

• Chemical Name: Phebestin
• CAS No.: 187402-73-9
• Molecular Formula: C₂₄H₃₁N₃O₅
• Molecular Weight: 441.527
• NSC Number: 702307
• DSSTox Substance ID: DTXSID20172056
• Nikkaji Number: J794.245A
• Wikidata: Q76279175
• Metabolomics Workbench ID: 126012
• ChEMBL ID: CHEMBL1991597
• Mol file: 187402-73-9.mol

Synonyms:(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl-valyl-phenylalanine;phebestin

Chemical Property of Phebestin

Chemical Property:

• Vapor Pressure: 6.55E-26mmHg at 25°C
• Boiling Point: 784.3°Cat760mmHg
• Flash Point: 428.1°C
• PSA: 141.75000
• Density: 1.234g/cm³
• LogP: 2.35230
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 441.22637110
• Heavy Atom Count: 32
• Complexity: 615

Purity/Quality:

98.5% ^*data from raw suppliers

N-((2S,3R)-3-AMINO-2-HYDROXY-1-OXO-4-PHENYLBUTY)-L-VA LYL-L-PHENYLALANINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Phebestin

There total 14 articles about Phebestin 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: 85.0%

(S)-2-[(S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyrylamino]-3-phenyl-propionic acid (217480-76-7) → 2-[2-(3-amino-2-hydroxy-4-phenylbutyrylamino)-3-methylbutyrylamino]-3-phenylpropionic acid (187402-73-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(03)01799-4

Reference yield:

2-(6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoylamino)-3-phenylpropionic acid benzyl ester (217480-75-6) → 2-[2-(3-amino-2-hydroxy-4-phenylbutyrylamino)-3-methylbutyrylamino]-3-phenylpropionic acid (187402-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / hydrogen / Pd/C / methanol / 3 h / 20 °C

2: 85 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

With hydrogen; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(03)01799-4

Reference yield:

(S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyric acid (612096-24-9) → 2-[2-(3-amino-2-hydroxy-4-phenylbutyrylamino)-3-methylbutyrylamino]-3-phenylpropionic acid (187402-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / EDAC; HOBt; DIPEA / dimethylformamide; CH₂Cl₂ / 12 h / 20 °C

2: 95 percent / hydrogen / Pd/C / methanol / 3 h / 20 °C

3: 85 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

With hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(03)01799-4

upstream raw materials:

(S)-2-[(S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyrylamino]-3-phenyl-propionic acid

(2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid

N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

(S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyric acid

Refernces

• 1、 Wasserman, Harry H.,Petersen, Anders K.,Xia, Mingde. "Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin". . p. 6771 - 6784. Retrieved 2007/10/03.