N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-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-ornithine
• CAS No.: 124620-55-9
• Molecular Formula: C₃₆H₄₄N₄O₉
• Molecular Weight: 676.767

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

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

Chemical Property:

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

There total 13 articles about N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-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: 66.0%

allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithinate (124620-54-8) → N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithine (124620-55-9)

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-ornithine (124620-55-9)

Guidance literature:

Multi-step reaction with 4 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

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:

(S)-5-(Acetyl-benzyloxy-amino)-2-amino-pentanoic acid allyl ester → N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithine (124620-55-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 66 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

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

DOI:10.1021/jm00107a013

upstream raw materials:

allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-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-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

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

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