N¹-benzyloxycarbonyl-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-D-leucyl)-1,8-octanediamine

Base Information

• Chemical Name: N¹-benzyloxycarbonyl-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-D-leucyl)-1,8-octanediamine
• CAS No.: 205874-64-2
• Molecular Formula: C₄₀H₆₃N₇O₈S
• Molecular Weight: 802.048

Synonyms:N¹-benzyloxycarbonyl-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-D-leucyl)-1,8-octanediamine

Chemical Property of N¹-benzyloxycarbonyl-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-D-leucyl)-1,8-octanediamine

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of N¹-benzyloxycarbonyl-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-D-leucyl)-1,8-octanediamine

There total 5 articles about N¹-benzyloxycarbonyl-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-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: 99.2%

Boc-Arg(Tos)-OH (13836-37-8) + N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine (175216-23-6) → N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-tosylarginyl-D-leucyl)-1,8-octanediamine (205874-64-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 5.5h;

DOI:10.1246/bcsj.71.699

Reference yield:

1,8-diaminooctan (373-44-4) → N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-tosylarginyl-D-leucyl)-1,8-octanediamine (205874-64-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 58.9 percent / triethylamine / diethyl ether / 0 °C

2: 100 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide; triethylamine / dimethylformamide / 0 - 20 °C

3: 94.2 percent / trifluoroacetic acid / CH₂Cl₂ / 0.25 h / 20 °C

4: 99.2 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 5.5 h / 0 - 20 °C

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

DOI:10.1246/bcsj.71.699

Reference yield:

N-Boc-D-Leu (16937-99-8,53296-34-7) → N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-tosylarginyl-D-leucyl)-1,8-octanediamine (205874-64-2)

Guidance literature:

Multi-step reaction with 3 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: 99.2 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 5.5 h / 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;

DOI:10.1246/bcsj.71.699

upstream raw materials:

Boc-Arg(Tos)-OH

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

1,8-diaminooctan

N-Boc-D-Leu

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