N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

Base Information

• Chemical Name: N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone
• CAS No.: 122314-19-6
• Molecular Formula: C₁₉H₂₉N₅O₅
• Molecular Weight: 407.47

Synonyms:N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

Chemical Property of N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

Chemical Property:

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Technology Process of N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

There total 2 articles about N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone 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:

Nα-(benzyloxycarbonyl)-Nδ-(tert-butoxycarbonyl)-L-ornithine methyl ester (32393-52-5) → Nα-(benzyloxycarbonyl)-Nδ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone (122314-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminum hydride (DIBAL) / toluene; hexane / 3 h / -50 °C

2: sodium acetate / ethanol; H₂O / 0.75 h / Heating

With sodium acetate; diisobutylaluminium hydride; In ethanol; hexane; water; toluene;

DOI:10.1021/jm00163a014

Reference yield:

((S)-4-tert-Butoxycarbonylamino-1-formyl-butyl)-carbamic acid benzyl ester (122314-14-1) + semicarbazide hydrochloride (563-41-7) → Nα-(benzyloxycarbonyl)-Nδ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone (122314-19-6)

Guidance literature:

With sodium acetate; In ethanol; water; for 0.75h; Yield given; Heating;

DOI:10.1021/jm00163a014

Reference yield:

Nα-(benzyloxycarbonyl)-Nδ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone (122314-19-6) → (benzyloxycarbonyl)-L-leucyl-L-valyl-Nδ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone (122314-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / H₂, 1 M hydrochloric acid / 10percent Pd/C / methanol / 3.5 h

2: triethylamine / CHCl₃ / 3 h / 0 °C

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In methanol; chloroform;

DOI:10.1021/jm00163a014

upstream raw materials:

((S)-4-tert-Butoxycarbonylamino-1-formyl-butyl)-carbamic acid benzyl ester

semicarbazide hydrochloride

N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithine methyl ester

Downstream raw materials:

(benzyloxycarbonyl)-L-leucyl-L-valyl-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

(benzyloxycarbonyl)-L-leucyl-L-leucyl-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

(benzyloxycarbonyl)-L-leucyl-L-phenylalanyl-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

(benzyloxycarbonyl)-L-phenylalanyl-L-leucyl-N^δ-(tert-butoxycarbonyl)-L-ornithinal semicarbazone

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