N¹-benzyloxycarbonyl-N⁵-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,5-pentanediamine

Base Information

• Chemical Name: N¹-benzyloxycarbonyl-N⁵-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,5-pentanediamine
• CAS No.: 205874-97-1
• Molecular Formula: C₅₁H₆₁N₇O₉S
• Molecular Weight: 948.153

Synonyms:N¹-benzyloxycarbonyl-N⁵-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,5-pentanediamine

Chemical Property of N¹-benzyloxycarbonyl-N⁵-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,5-pentanediamine

Chemical Property:

Purity/Quality:

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Technology Process of N¹-benzyloxycarbonyl-N⁵-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,5-pentanediamine

There total 5 articles about N¹-benzyloxycarbonyl-N⁵-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)-1,5-pentanediamine 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: 87.5%

Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosine (95015-69-3) + C26H38N6O5S → N1-benzyloxycarbonyl-N5-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosyl-Ng-tosylarginyl)-1,5-pentanediamine (205874-97-1)

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-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5) → N1-benzyloxycarbonyl-N5-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosyl-Ng-tosylarginyl)-1,5-pentanediamine (205874-97-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 87.5 percent / 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:

1,5-diaminopentane (462-94-2) → N1-benzyloxycarbonyl-N5-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosyl-Ng-tosylarginyl)-1,5-pentanediamine (205874-97-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 54.8 percent / triethylamine / diethyl ether / 0 °C

2: 99 percent / 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; N,N-diisopropylethylamine / dimethylformamide / 0 - 20 °C

3: 85.8 percent / trifluoroacetic acid / CH₂Cl₂ / 20 °C

4: 87.5 percent / 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; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Acylation / 3: deprotection / 4: Acylation;

DOI:10.1246/bcsj.71.699

upstream raw materials:

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

1,5-diaminopentane

N-benzyloxycarbonyl-O-benzyl-L-tyrosine

N-benzyloxycarbonyl-1,5-pentanediamine hydrochloride

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