ethyl N_α-benzyloxycarbonyl-N_ε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate

Base Information

• Chemical Name: ethyl N_α-benzyloxycarbonyl-N_ε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate
• CAS No.: 137271-91-1
• Molecular Formula: C₂₆H₃₉N₃O₇
• Molecular Weight: 505.612

Synonyms:ethyl N_α-benzyloxycarbonyl-N_ε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate

Chemical Property of ethyl N_α-benzyloxycarbonyl-N_ε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate

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Technology Process of ethyl N_α-benzyloxycarbonyl-N_ε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate

There total 2 articles about ethyl N_α-benzyloxycarbonyl-N_ε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate 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: 92.0%

Z-Lys(Boc)-OH (2389-60-8) + (S)-(+)-trans-4-amino-2-pentenoic acid ethyl ester (1006035-99-9) → ethyl Nα-benzyloxycarbonyl-Nε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate (137271-91-1)

Guidance literature:

With diethylphosphoryl cyanide; triethylamine; In N,N-dimethyl-formamide; for 24h; 0 deg C -> r. t.;

DOI:10.1016/S0040-4020(01)86557-1

Reference yield:

ethyl [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoate (104700-37-0) → ethyl Nα-benzyloxycarbonyl-Nε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate (137271-91-1)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 0.5 h / 0 °C

2: 92 percent / diethylphosphoryl cyanide (DEPC), Et₃N / dimethylformamide / 24 h / 0 deg C -> r. t.

With diethylphosphoryl cyanide; triethylamine; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86557-1

Reference yield:

ethyl Nα-benzyloxycarbonyl-Nε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate (137271-91-1) → (E)-(S)-4-((S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoylamino)-pent-2-enoic acid

Guidance literature:

With sodium hydroxide; In methanol; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86557-1

upstream raw materials:

Z-Lys(Boc)-OH

(S)-(+)-trans-4-amino-2-pentenoic acid ethyl ester

ethyl [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoate

Downstream raw materials:

(E)-(S)-4-((S)-6-Amino-2-benzyloxycarbonylamino-hexanoylamino)-pent-2-enoic acid

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