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

Base Information

• Chemical Name: benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-4-hydroxyphenylglycinate
• CAS No.: 130761-82-9
• Molecular Formula: C₆₅H₇₅N₇O₁₄
• Molecular Weight: 1178.35

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-4-hydroxyphenylglycinate 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:

Cbz-L-pGlu-OH (32159-21-0) → 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)

Guidance literature:

Multi-step reaction with 14 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

13: 74 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

14: triethylamine, 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

Reference yield:

N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → 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)

Guidance literature:

Multi-step reaction with 15 steps

1: dicyclohexylamine (DCHA) / tetrahydrofuran / 0 °C

2: 70percent perchloric acid / Ambient temperature

3: 100 percent / 1 M KOH / methanol

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

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

6: 71 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature

7: 81 percent / Zn, AcOH / 3 h / Irradiation

8: 100 percent / trifluoroacetic acid / 0.5 h / Ambient temperature

9: 54 percent / acetonitrile / 60 °C

10: 30percent HBr / CH₂Cl₂; acetic acid / 0.17 h

11: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

12: 66 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

13: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

14: 74 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

15: triethylamine, 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; N-cyclohexyl-cyclohexanamine; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; acetonitrile;

DOI:10.1021/jm00107a013

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → 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)

Guidance literature:

Multi-step reaction with 16 steps

1: DCC / tetrahydrofuran / 0 °C

2: dicyclohexylamine (DCHA) / tetrahydrofuran / 0 °C

3: 70percent perchloric acid / Ambient temperature

4: 100 percent / 1 M KOH / methanol

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

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

7: 71 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / Ambient temperature

8: 81 percent / Zn, AcOH / 3 h / Irradiation

9: 100 percent / trifluoroacetic acid / 0.5 h / Ambient temperature

10: 54 percent / acetonitrile / 60 °C

11: 30percent HBr / CH₂Cl₂; acetic acid / 0.17 h

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

13: 66 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

14: 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / CH₂Cl₂

15: 74 percent / O-benzylhydroxylamine, Pd(PPh₃)4 / CH₂Cl₂ / 5 h

16: triethylamine, 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; N-cyclohexyl-cyclohexanamine; dicyclohexyl-carbodiimide; 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-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

(R)-Amino-(4-hydroxy-phenyl)-acetic acid benzyl ester

N-benzyloxycarbonyl-L-glutamic acid

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

Downstream raw materials:

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

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