N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

Base Information

• Chemical Name: N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide
• CAS No.: 444154-88-5
• Molecular Formula: C₃₉H₄₈N₆O₉
• Molecular Weight: 744.845

Synonyms:N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

Chemical Property of N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

Chemical Property:

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Technology Process of N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

There total 2 articles about N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide 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-N2-methyl-N5-phenylmethylene-N5-oxide-L-ornithine (444154-65-8) + [(S)-4-Amino-4-((S)-1-hydroxy-2-oxo-piperidin-3-ylcarbamoyl)-butyl]-carbamic acid benzyl ester; compound with trifluoro-acetic acid → N5-benzyloxycarbonyl-(N2-benzyloxycarbonyl-N2-methyl-N5-phenylmethylene-N5-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-88-5)

Guidance literature:

With dmap; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jo0256078

Reference yield:

C20H22N2O5 → N5-benzyloxycarbonyl-(N2-benzyloxycarbonyl-N2-methyl-N5-phenylmethylene-N5-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaH / tetrahydrofuran / 24 h / 20 °C

2: 0.949 g / HOAt; EDC; DMAP / dimethylformamide / 0 - 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo0256078

Reference yield: 75.0%

N5-benzyloxycarbonyl-(N2-benzyloxycarbonyl-N2-methyl-N5-phenylmethylene-N5-oxide-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide (444154-88-5) → {(S)-1-[(S)-4-Benzyloxycarbonylamino-1-((S)-1-hydroxy-2-oxo-piperidin-3-ylcarbamoyl)-butylcarbamoyl]-4-hydroxyamino-butyl}-methyl-carbamic acid benzyl ester; hydrochloride

Guidance literature:

With hydroxylamine hydrochloride; In methanol; at 60 - 70 ℃; for 0.333333h;

DOI:10.1021/jo0256078

upstream raw materials:

N²-benzyloxycarbonyl-N²-methyl-N⁵-phenylmethylene-N⁵-oxide-L-ornithine

Downstream raw materials:

N⁵-benzyloxycarbonyl-(N²-benzyloxycarbonyl-N⁵-N,N-tert-butyloxycarbonyl-β-alanyl-β-alanyl-N⁵-hydroxy-N²-methyl-L-ornithyl)-N-[(S)-1-hydroxy-2-oxo-3-piperidyl]-L-ornithinamide

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