N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine

Base Information

• Chemical Name: N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine
• CAS No.: 205874-96-0
• Molecular Formula: C₅₉H₈₂N₆O₉
• Molecular Weight: 1019.33

Synonyms:N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine

Chemical Property of N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine

Chemical Property:

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Technology Process of N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine

There total 9 articles about N¹-benzyloxycarbonyl-N⁸-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine 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:

N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5) → N1-benzyloxycarbonyl-N8-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine (205874-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 78.3 percent / NaH / tetrahydrofuran / 0 - 20 °C

2: 348 mg / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 0 - 20 °C

With sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Methylation / 2: Acylation;

DOI:10.1246/bcsj.71.699

Reference yield:

Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosine (95015-69-3) + H-Leu-D-Leu-D-Leu-Oda-Z → N1-benzyloxycarbonyl-N8-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine (205874-96-0)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1246/bcsj.71.699

Reference yield:

N-Boc-D-Leu (16937-99-8,53296-34-7) → N1-benzyloxycarbonyl-N8-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosylleucyl-D-leucyl-D-leucyl)-1,8-octanediamine (205874-96-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide; triethylamine / dimethylformamide / 0 - 20 °C

2: 94.2 percent / trifluoroacetic acid / CH₂Cl₂ / 0.25 h / 20 °C

3: 99.7 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 0 - 20 °C

4: trifluoroacetic acid / CH₂Cl₂ / 20 °C

5: 679 mg / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 0 - 20 °C

6: trifluoroacetic acid / CH₂Cl₂ / 20 °C

7: 348 mg / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 0 - 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: deprotection / 3: Acylation / 4: deprotection / 5: Acylation / 6: deprotection / 7: Acylation;

DOI:10.1246/bcsj.71.699

upstream raw materials:

N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosine

N-Boc-D-Leu

N-benzyloxycarbonyl-O-benzyl-L-tyrosine

N¹-benzyloxycarbonyl-N⁸-D-leucyl-1,8-octanediamine

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