N-[(2R,4S,5S)-2-benzyl-5-{[N-(tert-butoxycarbonyl)-L-phenylalanyl]amino}-4-hydroxy-6-phenylhexanoyl]-L-leucyl-L-phenylalaninamide

Base Information

• Chemical Name: N-[(2R,4S,5S)-2-benzyl-5-{[N-(tert-butoxycarbonyl)-L-phenylalanyl]amino}-4-hydroxy-6-phenylhexanoyl]-L-leucyl-L-phenylalaninamide
• CAS No.: 132565-30-1
• Molecular Formula: C₄₈H₆₁N₅O₇
• Molecular Weight: 820.042

Synonyms:

Chemical Property of N-[(2R,4S,5S)-2-benzyl-5-{[N-(tert-butoxycarbonyl)-L-phenylalanyl]amino}-4-hydroxy-6-phenylhexanoyl]-L-leucyl-L-phenylalaninamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1078.8°Cat760mmHg
• Flash Point: 606.2°C
• Density: 1.173g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-[(2R,4S,5S)-2-benzyl-5-{[N-(tert-butoxycarbonyl)-L-phenylalanyl]amino}-4-hydroxy-6-phenylhexanoyl]-L-leucyl-L-phenylalaninamide

There total 4 articles about N-[(2R,4S,5S)-2-benzyl-5-{[N-(tert-butoxycarbonyl)-L-phenylalanyl]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:

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one (98818-41-8) → ((S)-1-{(1S,2S,4R)-1-Benzyl-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-2-hydroxy-5-phenyl-pentylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester (132565-30-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1 M LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

2: imidazole / dimethylformamide / 18 h / Ambient temperature

3: MeOH / 1 h

4: EDC, HOBt / dimethylformamide / pH = 8.0-9.0

5: tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

6: TFA / CH₂Cl₂ / 0.5 h / 0 °C

7: EDC, HOBt / dimethylformamide / 18 h / Ambient temperature; pH = 8.0-9.0

With 1H-imidazole; methanol; lithium hydroxide; tetrabutyl ammonium fluoride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00107a050

Reference yield:

5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid (98818-45-2) → ((S)-1-{(1S,2S,4R)-1-Benzyl-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-2-hydroxy-5-phenyl-pentylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester (132565-30-1)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 18 h / Ambient temperature

2: MeOH / 1 h

3: EDC, HOBt / dimethylformamide / pH = 8.0-9.0

4: tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

5: TFA / CH₂Cl₂ / 0.5 h / 0 °C

6: EDC, HOBt / dimethylformamide / 18 h / Ambient temperature; pH = 8.0-9.0

With 1H-imidazole; methanol; tetrabutyl ammonium fluoride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00107a050

Reference yield:

{(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) → ((S)-1-{(1S,2S,4R)-1-Benzyl-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-2-hydroxy-5-phenyl-pentylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester (132565-30-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

2: TFA / CH₂Cl₂ / 0.5 h / 0 °C

3: EDC, HOBt / dimethylformamide / 18 h / Ambient temperature; pH = 8.0-9.0

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00107a050

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(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

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

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