(3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

Base Information

• Chemical Name: (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione
• CAS No.: 131618-21-8
• Molecular Formula: C₅₃H₆₁Cl₆N₇O₁₄
• Molecular Weight: 1232.82

Synonyms:(3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

Chemical Property of (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

There total 15 articles about (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione 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:

N2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester (124620-52-6) → (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione (131618-21-8)

Guidance literature:

Multi-step reaction with 7 steps

1: CF₃COOH / CH₂Cl₂

2: diethyl ether

3: 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

4: Et₃N, EEDQ / CH₂Cl₂

5: 28 percent / 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

6: 70 percent / imidazole / methanol / 96 h

7: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1.) THF, 0 deg C, 30 min, 2.) CHCl₃, 4h

With 1H-imidazole; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00002a005

Reference yield:

C23H25Cl3N2O7 → (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione (131618-21-8)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether

2: 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

3: Et₃N, EEDQ / CH₂Cl₂

4: 28 percent / 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

5: 70 percent / imidazole / methanol / 96 h

6: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1.) THF, 0 deg C, 30 min, 2.) CHCl₃, 4h

With 1H-imidazole; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00002a005

Reference yield:

N-benzyloxyamine (622-33-3) → (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione (131618-21-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / pyridine / CH₂Cl₂ / 1 h

2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 13 h / Ambient temperature

3: CF₃COOH / CH₂Cl₂ / 1 h

4: Et₃N, EEDQ / CH₂Cl₂

5: 28 percent / 30percent HBr-HOAc / CH₂Cl₂ / 0.17 h

6: 70 percent / imidazole / methanol / 96 h

7: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1.) THF, 0 deg C, 30 min, 2.) CHCl₃, 4h

With pyridine; 1H-imidazole; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen bromide; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00002a005

upstream raw materials:

(3S,6S)-3-<3-propyl>-6-<3-propyl>-2,5-piperazinedione

2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine

N-benzyloxyamine

N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester

Downstream raw materials:

(3S,6S)-3-<3-2-acetyl-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-3-acetoxy-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

(3S,6S)-3-<3-2-acetyl-N⁵-(benzyloxy)-N⁵-formyl-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

foroxymithine

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