N-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine

Base Information

• Chemical Name: N-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine
• CAS No.: 75263-45-5
• Molecular Formula: C₄₇H₆₂N₆O₁₀
• Molecular Weight: 871.043

Synonyms:N-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine

Chemical Property of N-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine

Chemical Property:

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Technology Process of N-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine

There total 11 articles about N-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine 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: 65.0%

N-benzyloxycarbonyltryptophyl-Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine methyl ester (79385-59-4) → N-benzyloxycarbonyltryptophyl-Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine (75263-45-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 1h;

DOI:10.1039/P19810002040

Reference yield:

Z-Lys(Boc)-OH (2389-60-8) → N-benzyloxycarbonyltryptophyl-Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine (75263-45-5)

Guidance literature:

Multi-step reaction with 5 steps

1: dicyclohexylcarbodi-imide / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 10 deg C, 1 h

2: 61 percent / triethylamine / dimethylformamide

3: hydrogen / 10percent palladium-charcoal / methanol

4: dimethylformamide

5: 65 percent / 4 M NaOH / dioxane / 1 h

With sodium hydroxide; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1039/P19810002040

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → N-benzyloxycarbonyltryptophyl-Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine (75263-45-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / triethylamine / dimethylformamide / 1.) -5 deg C - 0 deg C, 1 h, 2.) room temperature, overnight

2: 10.3 g / hydrogen / 5percent palladium-charcoal / methanol; acetic acid / Ambient temperature

3: 61 percent / triethylamine / dimethylformamide

4: hydrogen / 10percent palladium-charcoal / methanol

5: dimethylformamide

6: 65 percent / 4 M NaOH / dioxane / 1 h

With sodium hydroxide; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1039/P19810002040

upstream raw materials:

N-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine methyl ester

Z-Lys(Boc)-OH

Z-Thr(Bu^t)-ONSu

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

Downstream raw materials:

tryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonyl-phenylalanine

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