N⁵-benzyloxycarbonyl-(N⁵-benzyloxy-N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N²-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

Base Information

• Chemical Name: N⁵-benzyloxycarbonyl-(N⁵-benzyloxy-N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N²-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide
• CAS No.: 444154-95-4
• Molecular Formula: C₅₇H₇₄N₈O₁₃
• Molecular Weight: 1079.26
• Mol file: 444154-95-4.mol

Synonyms:N⁵-benzyloxycarbonyl-(N⁵-benzyloxy-N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N²-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

Chemical Property of N⁵-benzyloxycarbonyl-(N⁵-benzyloxy-N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N²-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁵-benzyloxycarbonyl-(N⁵-benzyloxy-N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N²-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide

There total 10 articles about N⁵-benzyloxycarbonyl-(N⁵-benzyloxy-N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N²-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide 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:

C20H22N2O5 → N5-benzyloxycarbonyl-(N5-benzyloxy-N2-benzyloxycarbonyl-N5-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N2-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-95-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NH₂OH*HCl / methanol / 0.33 h / Heating

1.2: Et₃N; 3 Angstroem molecular sieves / methanol / 1 h / Heating

1.3: 65 percent / K₂CO₃ / dimethylformamide / 20 °C

2.1: 92 percent / HBr; AcOH / CH₂Cl₂ / 1 h / 20 °C

3.1: 94 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

4.1: 92 percent / TFA / CH₂Cl₂ / 0.67 h / 20 °C

5.1: 92 percent / HOAt; EDC / dimethylformamide / 20 °C

6.1: NH₂OH*HCl / methanol / 0.33 h / 60 - 70 °C

7.1: BOP; DMAP / dimethylformamide; acetonitrile / 20 °C

8.1: 266.1 mg / K₂CO₃ / dimethylformamide / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; hydrogen bromide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0256078

Reference yield:

Boc-Orn(Z)-OH (2480-93-5) → N5-benzyloxycarbonyl-(N5-benzyloxy-N2-benzyloxycarbonyl-N5-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N2-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-95-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

2: 92 percent / TFA / CH₂Cl₂ / 0.67 h / 20 °C

3: 92 percent / HOAt; EDC / dimethylformamide / 20 °C

4: NH₂OH*HCl / methanol / 0.33 h / 60 - 70 °C

5: BOP; DMAP / dimethylformamide; acetonitrile / 20 °C

6: 266.1 mg / K₂CO₃ / dimethylformamide / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0256078

Reference yield:

benzyl bromide (100-39-0) → N5-benzyloxycarbonyl-(N5-benzyloxy-N2-benzyloxycarbonyl-N5-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N2-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-95-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NH₂OH*HCl / methanol / 0.33 h / Heating

1.2: Et₃N; 3 Angstroem molecular sieves / methanol / 1 h / Heating

1.3: 65 percent / K₂CO₃ / dimethylformamide / 20 °C

2.1: 92 percent / HBr; AcOH / CH₂Cl₂ / 1 h / 20 °C

3.1: 94 percent / HOAt; EDC; DMAP / CH₂Cl₂ / 20 °C

4.1: 92 percent / TFA / CH₂Cl₂ / 0.67 h / 20 °C

5.1: 92 percent / HOAt; EDC / dimethylformamide / 20 °C

6.1: NH₂OH*HCl / methanol / 0.33 h / 60 - 70 °C

7.1: BOP; DMAP / dimethylformamide; acetonitrile / 20 °C

8.1: 266.1 mg / K₂CO₃ / dimethylformamide / 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; hydrogen bromide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0256078

upstream raw materials:

Boc-Orn(Z)-OH

benzyl bromide

(S)-3-benzyloxycarbonylamino-1-benzyloxypiperidin-2-one

N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithine

Downstream raw materials:

N⁵-benzyloxycarbonyl-(N⁵-benzyloxy-N²-benzyloxycarbonyl-N⁵,N-β-alanyl-β-alanyl-N²-methyl-L-ornithyl)-N-[(S)-1-benzyloxy-2-oxo-3-piperidyl]-L-ornithinamide