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

Base Information

• Chemical Name: allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithinate
• CAS No.: 124620-53-7
• Molecular Formula: C₂₅H₃₀N₂O₆
• Molecular Weight: 454.523
• Mol file: 124620-53-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-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: 78.0%

N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithine (89969-29-9) → allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithinate (124620-53-7)

Guidance literature:

In acetonitrile; at 50 ℃;

DOI:10.1021/jm00164a001

Reference yield: 54.0%

N,N'-diisopropyl-O-allylisourea (3116-52-7) + N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithine (89969-29-9) → allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithinate (124620-53-7)

Guidance literature:

In acetonitrile; at 60 ℃;

DOI:10.1021/jm00107a013

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → allyl N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithinate (124620-53-7)

Guidance literature:

Multi-step reaction with 10 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

With potassium hydroxide; sodium tetrahydroborate; perchloric acid; di-isopropyl azodicarboxylate; acetic acid; triethylamine; N-cyclohexyl-cyclohexanamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1021/jm00107a013

upstream raw materials:

N,N'-diisopropyl-O-allylisourea

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

N-benzyloxycarbonyl-L-glutamic acid

Cbz-L-pGlu-OH

Downstream raw materials:

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

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

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

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