(E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene

Base Information

• Chemical Name: (E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene
• CAS No.: 1372138-82-3
• Molecular Formula: C₂₈H₃₆N₂O₅
• Molecular Weight: 480.604

Synonyms:(E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene

Chemical Property of (E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene

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Technology Process of (E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene

There total 2 articles about (E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene 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: 65.0%

N-Cbz-2-hydroxypiperidine + dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate (176504-90-8) → (E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene (1372138-82-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at 25 ℃; for 16h;

DOI:10.1021/jm3001136

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene (1372138-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - -30 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 16 h / 25 °C

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1021/jm3001136

Reference yield: 94.0%

(E,2S)-9-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenylnon-4-ene (1372138-82-3) → (E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenylnon-4-ene (1372138-78-7)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In ethanol; at -78 - -60 ℃; Inert atmosphere;

DOI:10.1021/jm3001136

upstream raw materials:

dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

(1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-piperidin-2-yl)butane-1,2-diol

C₅₁H₆₆N₈O₈

(E,2S,3R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-hydroxy-1-phenylnon-4-ene

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