N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)bis(4-methylphenyl)methanamine

Base Information

• Chemical Name: N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)bis(4-methylphenyl)methanamine
• CAS No.: 205875-00-9
• Molecular Formula: C₅₃H₅₈N₆O₇S
• Molecular Weight: 923.146

Synonyms:N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)bis(4-methylphenyl)methanamine

Chemical Property of N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)bis(4-methylphenyl)methanamine

Chemical Property:

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Technology Process of N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)bis(4-methylphenyl)methanamine

There total 7 articles about N-(N^α-benzyloxycarbonyl-N^α-methyl-O-benzyltyrosyl-N^g-tosylarginyl)bis(4-methylphenyl)methanamine 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: 94.6%

Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosine (95015-69-3) + H-Arg(Ts)-NHBzh(Me)2 → N-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosyl-Ng-tosylarginyl)bis(4-methylphenyl)methanamine (205875-00-9)

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) → N-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosyl-Ng-tosylarginyl)bis(4-methylphenyl)methanamine (205875-00-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 94.6 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:

bis(p-methylphenyl)-methanone (611-97-2) → N-(Nα-benzyloxycarbonyl-Nα-methyl-O-benzyltyrosyl-Ng-tosylarginyl)bis(4-methylphenyl)methanamine (205875-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 91.7 percent / formic acid / 168 °C

2: 98 percent / aq. HCl; formic acid / 0.5 h / 75 °C

3: 100 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 0 - 20 °C

4: trifluoroacetic acid / CH₂Cl₂ / 20 °C

5: 94.6 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole / dimethylformamide / 0 - 20 °C

With hydrogenchloride; formic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Acylation / 4: deprotection / 5: Acylation;

DOI:10.1246/bcsj.71.699

upstream raw materials:

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

bis(p-methylphenyl)-methanone

4,4'-dimethyl-benzhydrylamine

Boc-Arg(Tos)-OH

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