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

Base Information

• Chemical Name: N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine
• CAS No.: 130761-84-1
• Molecular Formula: C₂₉H₄₅N₇O₁₂
• Molecular Weight: 683.716

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

Chemical Property of N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine

There total 20 articles about N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine 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: 94.0%

benzyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-D-4-hydroxyphenylglycinate (130761-82-9) → N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine (130761-84-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; for 3h;

DOI:10.1021/jm00107a013

Reference yield:

N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithine (89969-29-9) → N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine (130761-84-1)

Guidance literature:

Multi-step reaction with 8 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

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

8: 94 percent / H₂ / 10percent Pd/C / methanol; H₂O / 3 h

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

DOI:10.1021/jm00107a013

Reference yield:

N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithine 1-tert-butyl ester (92412-96-9) → N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine (130761-84-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / trifluoroacetic acid / 0.5 h / Ambient temperature

2: 54 percent / acetonitrile / 60 °C

3: 30percent HBr / CH₂Cl₂; acetic acid / 0.17 h

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

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

6: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

7: 74 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

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

9: 94 percent / H₂ / 10percent Pd/C / methanol; H₂O / 3 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-benzyloxyamine; hydrogen bromide; hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1021/jm00107a013

upstream raw materials:

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

N-benzyloxycarbonyl-L-glutamic acid

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

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

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