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

Base Information

• Chemical Name: benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate
• CAS No.: 1423738-99-1
• Molecular Formula: C₃₀H₄₆N₄O₄
• Molecular Weight: 526.72
• Mol file: 1423738-99-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate 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: 92.0%

benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-18-{[(4-methylphenyl)sulfonyl]oxy}octadeca-4,6-dienoate (1423738-96-8) → benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate (1423738-99-1)

Guidance literature:

With sodium azide; tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 60 ℃; for 2h; Inert atmosphere;

DOI:10.1007/s00726-012-1349-0

Reference yield:

(12-hydroxydodecyl)triphenylphosphonium bromide (97780-30-8) → benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate (1423738-99-1)

Guidance literature:

Multi-step reaction with 3 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

3.1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere

With dmap; sodium azide; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.2: |Wittig Olefination;

DOI:10.1007/s00726-012-1349-0

Reference yield:

(S)-benzyl-4-oxo-2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate (124994-66-7) → benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate (1423738-99-1)

Guidance literature:

Multi-step reaction with 4 steps

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

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

2.2: 2 h / -60 °C / Inert atmosphere

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

4.1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere

With dmap; sodium azide; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: |Wittig Olefination / 2.2: |Wittig Olefination;

DOI:10.1007/s00726-012-1349-0

upstream raw materials:

12-bromododecanol

(12-hydroxydodecyl)triphenylphosphonium bromide

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

Downstream raw materials:

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