β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester

Base Information

• Chemical Name: β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester
• CAS No.: 368443-60-1
• Molecular Formula: C₄₅H₅₀F₅N₅O₁₄
• Molecular Weight: 979.909
• Mol file: 368443-60-1.mol

Synonyms:β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester

Chemical Property of β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester

There total 15 articles about β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester 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: 86.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] triester (368443-59-8) → β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester (368443-60-1)

Guidance literature:

With 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1039/b100401h

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester (368443-60-1)

Guidance literature:

Multi-step reaction with 7 steps

1: NMM / tetrahydrofuran / 0.08 h / -15 °C

2: 5.09 g / NMM / tetrahydrofuran / 3 h / 20 °C

3: 95 percent / pyrrolidine / (Ph₃P)4Pd⁽⁰⁾ / CH₂Cl₂ / 1 h / 20 °C

4: NMM / tetrahydrofuran; dimethylformamide / 0.08 h / -15 °C

5: 2.78 g / NMM / tetrahydrofuran; dimethylformamide / 4 h / 20 °C

6: 100 percent / pyrrolidine / (Ph₃P)4Pd⁽⁰⁾ / CH₂Cl₂ / 0.75 h / 20 °C

7: 86 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide / CH₂Cl₂ / 15 h / 20 °C

With pyrrolidine; 4-methyl-morpholine; 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b100401h

Reference yield:

Boc-Phe-O-COO-isoBu (67729-36-6,60398-40-5) → β-pentafluorophenyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester (368443-60-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 5.09 g / NMM / tetrahydrofuran / 3 h / 20 °C

2: 95 percent / pyrrolidine / (Ph₃P)4Pd⁽⁰⁾ / CH₂Cl₂ / 1 h / 20 °C

3: NMM / tetrahydrofuran; dimethylformamide / 0.08 h / -15 °C

4: 2.78 g / NMM / tetrahydrofuran; dimethylformamide / 4 h / 20 °C

5: 100 percent / pyrrolidine / (Ph₃P)4Pd⁽⁰⁾ / CH₂Cl₂ / 0.75 h / 20 °C

6: 86 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide / CH₂Cl₂ / 15 h / 20 °C

With pyrrolidine; 4-methyl-morpholine; 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b100401h

upstream raw materials:

2,3,4,5,6-pentafluorophenol

(2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] triester

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Phe-O-COO-isoBu

Downstream raw materials:

cyclo{-[(R)-Asp]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-}

cyclo{-[(R)-Asp α-OBn]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-}

(5R,9S,12R,16R)-9-Benzyl-12-(4-benzyl-piperidine-1-carbonyl)-1-methyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaaza-cyclononadecane-5,16-dicarboxylic acid dimethyl ester