Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate

Base Information

• Chemical Name: Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate
• CAS No.: 124650-79-9
• Molecular Formula: C₅₃H₆₆N₆O₁₂
• Molecular Weight: 979.14

Synonyms:Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate

Chemical Property of Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate

There total 12 articles about Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 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:

N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithine (89969-29-9) → Allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithinate (124650-79-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 54 percent / acetonitrile / 60 °C

2: 30percent HBr / CH₂Cl₂; acetic acid / 0.17 h

3: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

4: 66 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

5: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-benzyloxyamine; hydrogen bromide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/jm00107a013

Reference yield:

allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithinate (124620-53-7) → Allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithinate (124650-79-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 30percent HBr / CH₂Cl₂; acetic acid / 0.17 h

2: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

3: 66 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

4: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-benzyloxyamine; hydrogen bromide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; acetic acid;

DOI:10.1021/jm00107a013

Reference yield:

Cbz-L-pGlu-OH (32159-21-0) → Allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithinate (124650-79-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 70percent perchloric acid / Ambient temperature

2: 100 percent / 1 M KOH / methanol

3: triethylamine / tetrahydrofuran / 1 h / 0 °C

4: sodium borohydride / tetrahydrofuran; H₂O / 4 h / Ambient temperature

5: 71 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature

6: 81 percent / Zn, AcOH / 3 h / Irradiation

7: 100 percent / trifluoroacetic acid / 0.5 h / Ambient temperature

8: 54 percent / acetonitrile / 60 °C

9: 30percent HBr / CH₂Cl₂; acetic acid / 0.17 h

10: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

11: 66 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

12: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

With potassium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; N-benzyloxyamine; di-isopropyl azodicarboxylate; hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1021/jm00107a013

upstream raw materials:

N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

N-benzyloxycarbonyl-L-glutamic acid

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

Cbz-L-pGlu-OH

Downstream raw materials:

(N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-L-seryl-1,4-dibenzyl-D-aspartate

N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine

benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-L-serinate

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