3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester

Base Information

• Chemical Name: 3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester
• CAS No.: 80682-12-8
• Molecular Formula: C₃₄H₄₁N₇O₁₁S
• Molecular Weight: 755.806
• Mol file: 80682-12-8.mol

Synonyms:3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester

Chemical Property of 3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester

There total 11 articles about 3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester 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:

(S)-4-Amino-4-[(S)-3-{(R)-2-benzyloxycarbonylamino-2-[(2,4,5-trichloro-phenoxycarbonylmethyl)-carbamoyl]-ethylsulfanylcarbonyl}-1-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-propylcarbamoyl]-butyric acid benzyl ester (80682-11-7) → 3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester (80682-12-8)

Guidance literature:

With pyridine; In tetrahydrofuran; at 25 ℃; for 24h; Yield given;

DOI:10.1021/ja00414a075

Reference yield:

Boc-Glu(OBzl)-OH (13574-13-5) → 3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester (80682-12-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 deg C, 5 min, 2.) -15 deg C, 0.5 h; 25 deg C

2: 96 percent / hydrogen, formic acid / Pd black / methanol / 0.25 h

3: CF₃CO₂H / CH₂Cl₂ / 0.5 h / 25 °C

4: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 deg C, 5 min, 2.) -15 deg C, 0.5 h; 25 deg C

5: N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 25 deg C, 18 h

6: triethylamine / dimethylformamide / 4 h / 40 °C

7: N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 25 deg C, 18 h

8: CF₃CO₂H / CH₂Cl₂ / 0.5 h / 25 °C

9: pyridine / tetrahydrofuran / 24 h / 25 °C

With 4-methyl-morpholine; pyridine; formic acid; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; palladium; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00414a075

Reference yield:

[N-α-Boc-O-γ-(benzyl)glutamyl]asparagyl-NH2 (80682-04-8) → 3-[(3R,9S,12S)-3-Benzyloxycarbonylamino-12-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-4,7,10,15-tetraoxo-1-thia-5,8,11-triaza-cyclopentadec-9-yl]-propionic acid benzyl ester (80682-12-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / hydrogen, formic acid / Pd black / methanol / 0.25 h

2: CF₃CO₂H / CH₂Cl₂ / 0.5 h / 25 °C

3: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) THF, -15 deg C, 5 min, 2.) -15 deg C, 0.5 h; 25 deg C

4: N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 25 deg C, 18 h

5: triethylamine / dimethylformamide / 4 h / 40 °C

6: N,N'-dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 25 deg C, 18 h

7: CF₃CO₂H / CH₂Cl₂ / 0.5 h / 25 °C

8: pyridine / tetrahydrofuran / 24 h / 25 °C

With 4-methyl-morpholine; pyridine; formic acid; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; palladium; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00414a075

upstream raw materials:

(S)-4-Amino-4-[(S)-3-{(R)-2-benzyloxycarbonylamino-2-[(2,4,5-trichloro-phenoxycarbonylmethyl)-carbamoyl]-ethylsulfanylcarbonyl}-1-((S)-1,2-dicarbamoyl-ethylcarbamoyl)-propylcarbamoyl]-butyric acid benzyl ester

Boc-Glu(OBzl)-OH

N,N'-bis(benzyloxycarbonyl)-L-cystine

Z-Cys(SH)-Gly-OH