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

Base Information

• Chemical Name: (N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine
• CAS No.: 124620-56-0
• Molecular Formula: C₅₀H₆₂N₆O₁₂
• Molecular Weight: 939.075
• Mol file: 124620-56-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 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: 74.0%

Allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithinate (124650-79-9) → (N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl)-(N5-acetyl-N5-(benzyloxy)-L-ornithyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine (124620-56-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-benzyloxyamine; In dichloromethane;

DOI:10.1021/jm00164a001

Reference yield:

N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithine (89969-29-9) → (N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl)-(N5-acetyl-N5-(benzyloxy)-L-ornithyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine (124620-56-0)

Guidance literature:

Multi-step reaction with 6 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

6: 74 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

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) → (N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl)-(N5-acetyl-N5-(benzyloxy)-L-ornithyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine (124620-56-0)

Guidance literature:

Multi-step reaction with 5 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

5: 74 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

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

DOI:10.1021/jm00107a013

upstream raw materials:

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

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 succinimido ester

4-nitrobenzyl 7β-<5-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-4-(benzyloxy)phenylglycyl>amino>-1-carba-3-chloro-3-cephem-4-carboxylate

benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-4-hydroxyphenylglycinate

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