N²-5-(benzyloxy)-L-ornithinyl>-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester

Base Information

• Chemical Name: N²-5-(benzyloxy)-L-ornithinyl>-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester
• CAS No.: 131635-36-4
• Molecular Formula: C₂₈H₃₇Cl₃N₄O₇
• Molecular Weight: 647.983

Synonyms:N²-5-(benzyloxy)-L-ornithinyl>-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester

Chemical Property of N²-5-(benzyloxy)-L-ornithinyl>-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester

Chemical Property:

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Technology Process of N²-5-(benzyloxy)-L-ornithinyl>-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester

There total 9 articles about N²-5-(benzyloxy)-L-ornithinyl>-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-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:

N2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester (124620-52-6) → N2-5-(benzyloxy)-L-ornithinyl>-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester (131635-36-4)

Guidance literature:

Multi-step reaction with 5 steps

1: CF₃COOH / CH₂Cl₂

2: diethyl ether

3: 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

4: Et₃N, EEDQ / CH₂Cl₂

5: 28 percent / 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

With hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane;

DOI:10.1021/jo00002a005

Reference yield:

N-benzyloxyamine (622-33-3) → N2-5-(benzyloxy)-L-ornithinyl>-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester (131635-36-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / pyridine / CH₂Cl₂ / 1 h

2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 13 h / Ambient temperature

3: CF₃COOH / CH₂Cl₂ / 1 h

4: Et₃N, EEDQ / CH₂Cl₂

5: 28 percent / 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

With pyridine; hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00002a005

Reference yield:

(S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate (124620-51-5) → N2-5-(benzyloxy)-L-ornithinyl>-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithine 1-methyl ester (131635-36-4)

Guidance literature:

Multi-step reaction with 4 steps

1: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 13 h / Ambient temperature

2: CF₃COOH / CH₂Cl₂ / 1 h

3: Et₃N, EEDQ / CH₂Cl₂

4: 28 percent / 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

With hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00002a005

upstream raw materials:

N-benzyloxyamine

N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester

(S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate

N-(allyloxycarbonyl)-O-benzylhydroxylamine

Downstream raw materials:

(3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

(3S,6S)-3-<3-2-acetyl-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-3-acetoxy-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

(3S,6S)-3-<3-propyl>-6-<3-propyl>-2,5-piperazinedione

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