N-(benzyloxycarbonyl)-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester
• CAS No.: 849599-71-9
• Molecular Formula: C₃₄H₄₈N₄O₈
• Molecular Weight: 640.777

Synonyms:N-(benzyloxycarbonyl)-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

Chemical Property of N-(benzyloxycarbonyl)-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

Chemical Property:

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Technology Process of N-(benzyloxycarbonyl)-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

There total 4 articles about N-(benzyloxycarbonyl)-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester 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: 75.0%

Z-Lys(Boc)-OH (2389-60-8) + L-valyl-L-phenylalanine methyl ester (39614-17-0,128557-46-0,145313-30-0) → N-(benzyloxycarbonyl)-Nε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester (849599-71-9)

Guidance literature:

Z-Lys(Boc)-OH; With 2,6-dimethylpyridine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); 6-chloro-1-hydroxybenzotriazole; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

L-valyl-L-phenylalanine methyl ester; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja045558b

Reference yield:

t-Boc-L-valine (13734-41-3) → N-(benzyloxycarbonyl)-Nε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester (849599-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HCTU; Cl-HOBt; 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0.17 h / 0 °C

1.2: 97 percent / 2,6-lutidine / CH₂Cl₂; dimethylformamide

2.1: CF₃CO₂H / CH₂Cl₂ / 0 °C

3.1: HCTU; Cl-HOBt; 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0.17 h / 0 °C

3.2: 75 percent / CH₂Cl₂; dimethylformamide

With 2,6-dimethylpyridine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); 6-chloro-1-hydroxybenzotriazole; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja045558b

Reference yield:

N-tert-butoxycarbonyl-L-valyl-L-phenylalanine methyl ester (20902-47-0) → N-(benzyloxycarbonyl)-Nε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester (849599-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CF₃CO₂H / CH₂Cl₂ / 0 °C

2.1: HCTU; Cl-HOBt; 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0.17 h / 0 °C

2.2: 75 percent / CH₂Cl₂; dimethylformamide

With 2,6-dimethylpyridine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); 6-chloro-1-hydroxybenzotriazole; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja045558b

upstream raw materials:

Z-Lys(Boc)-OH

L-valyl-L-phenylalanine methyl ester

t-Boc-L-valine

N-tert-butoxycarbonyl-L-valyl-L-phenylalanine methyl ester

Downstream raw materials:

5-acetylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonylamino-2-[4-methoxybenzyl]-2H-pyrazole-3-carbonyl-N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

N^ε-(tert-butyloxycarbonyl)-(S)-lysinyl-(S)-valinyl-(S)-phenylalanine methyl ester

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