N^α-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester

Base Information

• Chemical Name: N^α-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester
• CAS No.: 79385-68-5
• Molecular Formula: C₄₃H₆₅N₅O₉Si
• Molecular Weight: 824.103

Synonyms:N^α-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester

Chemical Property of N^α-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester

Chemical Property:

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Technology Process of N^α-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester

There total 7 articles about N^α-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl 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: 65.0%

Z-Trp-OBt (62120-76-7) + Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester hydrochloride (79385-71-0) → Nα-benzyloxycarbonyltryptophyl-Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester (79385-68-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; 1.) 0 deg C, 1 h, 2.) 8 deg C, 18 h;

DOI:10.1039/P19810002040

Reference yield:

Z-Lys(Boc)-OH (2389-60-8) → Nα-benzyloxycarbonyltryptophyl-Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester (79385-68-5)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 65 percent / triethylamine / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 8 deg C, 18 h

3: 13.1 g / hydrogen, acetic acid / 10percent palladium-charcoal / propan-2-ol / 16 h / Ambient temperature

4: 65 percent / triethylamine / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 8 deg C, 18 h

With hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1039/P19810002040

Reference yield:

Z-Thr(But)-OTmse (65903-67-5) → Nα-benzyloxycarbonyltryptophyl-Nε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester (79385-68-5)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen, acetic acid / 10percent palladium-charcoal / propan-2-ol / 3 h / Ambient temperature

2: 65 percent / triethylamine / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 8 deg C, 18 h

3: 13.1 g / hydrogen, acetic acid / 10percent palladium-charcoal / propan-2-ol / 16 h / Ambient temperature

4: 65 percent / triethylamine / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 8 deg C, 18 h

With hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1039/P19810002040

upstream raw materials:

Z-Trp-OBt

N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine 2-trimethylsilylethyl ester hydrochloride

Z-Lys(Boc)-OH

Z-Thr(Bu^t)-OTmse

Downstream raw materials:

N^α-benzyloxycarbonyltryptophyl-N^ε-t-butoxycarbonyl-lysyl-O-t-butylthreonine

Bpoc-Asn-Phe-Phe-Trp-Lys(Boc)-Thr(Bu^t)-OH

Bpoc-Asn-Phe(I)-Phe-Trp-Lys(Boc)-Thr(Bu^t)-OH

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