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

Base Information

• Chemical Name: cyclo{-[(R)-Asp]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-}
• CAS No.: 368443-62-3
• Molecular Formula: C₂₇H₃₅N₅O₁₁
• Molecular Weight: 605.602
• Mol file: 368443-62-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about cyclo{-[(R)-Asp]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-} 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:

cyclo{-[(R)-Asp α-OBn]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-} (368443-61-2) → cyclo{-[(R)-Asp]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-} (368443-62-3)

Guidance literature:

With hydrogen; 5percent Pd/C; In methanol; acetic acid; for 18h;

DOI:10.1039/b100401h

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → cyclo{-[(R)-Asp]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-} (368443-62-3)

Guidance literature:

Multi-step reaction with 10 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

8: CH₂Cl₂ / 1 h

9: 260 mg / DIPEA / CH₂Cl₂ / 168 h / 20 °C

10: H₂ / 5percent Pd/C / acetic acid; methanol / 18 h

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

DOI:10.1039/b100401h

Reference yield:

Boc-Phe-O-COO-isoBu (67729-36-6,60398-40-5) → cyclo{-[(R)-Asp]-β-[(R)-Glu α-OMe]-γ-Sar-[(R)-Asp α-OMe]-β-(S)-Phe-} (368443-62-3)

Guidance literature:

Multi-step reaction with 9 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

7: CH₂Cl₂ / 1 h

8: 260 mg / DIPEA / CH₂Cl₂ / 168 h / 20 °C

9: H₂ / 5percent Pd/C / acetic acid; methanol / 18 h

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

DOI:10.1039/b100401h

upstream raw materials:

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

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Phe-O-COO-isoBu

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

Downstream raw materials:

(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