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

Base Information

• Chemical Name: (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] triester
• CAS No.: 368443-59-8
• Molecular Formula: C₃₉H₅₁N₅O₁₄
• Molecular Weight: 813.859
• Mol file: 368443-59-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] triester 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: 100.0%

β-allyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester (368443-58-7) → (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] triester (368443-59-8)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1039/b100401h

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] triester (368443-59-8)

Guidance literature:

Multi-step reaction with 6 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

With pyrrolidine; 4-methyl-morpholine; 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) → (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] triester (368443-59-8)

Guidance literature:

Multi-step reaction with 5 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

With pyrrolidine; 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b100401h

upstream raw materials:

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

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Phe-O-COO-isoBu

(N-tert-butoxycarbonyl)-[α-methyl (2R)-glutamyl]-γ-sarcosine

Downstream raw materials:

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

(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

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

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