N-{(2r,4s,5s)-2-Benzyl-5-[(Tert-Butoxycarbonyl)amino]-4-Hydroxy-6-Phenylhexanoyl}-L-Leucyl-L-Phenylalaninamide

Base Information

• Chemical Name: N-{(2r,4s,5s)-2-Benzyl-5-[(Tert-Butoxycarbonyl)amino]-4-Hydroxy-6-Phenylhexanoyl}-L-Leucyl-L-Phenylalaninamide
• CAS No.: 126409-24-3
• Molecular Formula: C39H52 N4 O6
• Molecular Weight: 672.865
• DSSTox Substance ID: DTXSID70155177
• Nikkaji Number: J380.516F
• Wikidata: Q27454565
• ChEMBL ID: CHEMBL289195

Synonyms:L 682679;L-682,679;L-682679

Chemical Property of N-{(2r,4s,5s)-2-Benzyl-5-[(Tert-Butoxycarbonyl)amino]-4-Hydroxy-6-Phenylhexanoyl}-L-Leucyl-L-Phenylalaninamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 938.5°Cat760mmHg
• Flash Point: 521.4°C
• Density: 1.155g/cm³
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 19
• Exact Mass: 672.38868539
• Heavy Atom Count: 49
• Complexity: 1030

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)N)NC(=O)C(CC2=CC=CC=C2)CC(C(CC3=CC=CC=C3)NC(=O)OC(C)(C)C)O
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N)NC(=O)[C@H](CC2=CC=CC=C2)C[C@@H]([C@H](CC3=CC=CC=C3)NC(=O)OC(C)(C)C)O

Technology Process of N-{(2r,4s,5s)-2-Benzyl-5-[(Tert-Butoxycarbonyl)amino]-4-Hydroxy-6-Phenylhexanoyl}-L-Leucyl-L-Phenylalaninamide

There total 30 articles about N-{(2r,4s,5s)-2-Benzyl-5-[(Tert-Butoxycarbonyl)amino]-4-Hydroxy-6-Phenylhexanoyl}-L-Leucyl-L-Phenylalaninamide 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: 94.0%

{(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester (126410-32-0) → {(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2S)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester (126409-24-3,292632-98-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1055/s-2003-37649

Reference yield:

α-bromo-p-toluidine (63516-03-0) → {(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2S)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester (126409-24-3,292632-98-5)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOEt / ethanol / 18 h / Ambient temperature

2: aq. LiOH / ethanol / 5 h

3: toluene / 24 h / Heating

4: aq. LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

5: 1.) imidazole / 1.) DMF, RT, 24 h, 2.) DMF, MeOH, RT, 4 h

6: EDC*HCl, HOBt, Et₃N / dimethylformamide / 24 h / Ambient temperature

7: tetrabutylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature

With 1H-imidazole; lithium hydroxide; tetrabutyl ammonium fluoride; sodium ethanolate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00088a004

Reference yield:

N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid (98818-51-0) → {(1S)-benzyl-(4R)-[1-((1S)-carbamoyl-2-phenyl-ethylcarbamoyl)-(1S)-3-methyl-butyl-carbamoyl]-(2S)-hydroxy-5-phenyl-pentyl} carbamic acid tert-butyl ester (126409-24-3,292632-98-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / dimethylformamide / 15 h / 20 °C

2: 94 percent / Bu₄NF / tetrahydrofuran / 48 h / 20 °C

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1055/s-2003-37649

upstream raw materials:

{(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

(1S,4R)-{1-benzyl-4-[1-(1S)-carbamoyl-(2-phenylethylcarbamoyl)-(1S)-3-methylbutylcarbamoyl]-2-oxo-5-phenylpentyl}carbamic acid tert-butyl ester

N-tert-butoxycarbonyl-L-leucine

L-Phenylalanine amide

Downstream raw materials:

(1S,4R)-{1-benzyl-4-[1-(1S)-carbamoyl-(2-phenylethylcarbamoyl)-(1S)-3-methylbutylcarbamoyl]-2-oxo-5-phenylpentyl}carbamic acid tert-butyl ester

(5S)-(tert-butoxycarbonylamino)-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl-L-leucy-L-phenylalaninamide

L-364,505

(2R,4S,5S)-5-Amino-2-benzyl-4-hydroxy-6-phenyl-hexanoic acid [(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butyl]-amide

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