benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate

Base Information

• Chemical Name: benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate
• CAS No.: 1423738-88-8
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 1423738-88-8.mol

Synonyms:benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate

Chemical Property of benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate

There total 1 articles about benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate 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:

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester (30925-18-9) → benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate (1423738-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide; pyridine / acetonitrile; tetrahydrofuran / 1 h / -30 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: toluene / 3.5 h / 70 °C / Inert atmosphere

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; toluene; acetonitrile; 2.1: |Wittig Olefination;

DOI:10.1007/s00726-012-1349-0

Reference yield: 65.0%

benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate (1423738-88-8) + (12-hydroxydodecyl)triphenylphosphonium bromide (97780-30-8) → benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate (1423738-93-5)

Guidance literature:

(12-hydroxydodecyl)triphenylphosphonium bromide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -60 ℃; for 0.666667h; Inert atmosphere;

benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate; In tetrahydrofuran; at -60 ℃; for 2h; Inert atmosphere;

DOI:10.1007/s00726-012-1349-0

Reference yield:

benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate (1423738-88-8) → benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-18-{[(4-methylphenyl)sulfonyl]oxy}octadeca-4,6-dienoate (1423738-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -60 °C / Inert atmosphere

1.2: 2 h / -60 °C / Inert atmosphere

2.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere

With dmap; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.2: |Wittig Olefination;

DOI:10.1007/s00726-012-1349-0

upstream raw materials:

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

Downstream raw materials:

benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-18-{[(4-methylphenyl)sulfonyl]oxy}octadeca-4,6-dienoate

benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate

benzyl (2S)-2,18-bis[(tert-butoxycarbonyl)amino]octadeca-4,6-dienoate