(4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester

Base Information

• Chemical Name: (4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester
• CAS No.: 155089-08-0
• Molecular Formula: C₂₇H₄₃NO₅Si
• Molecular Weight: 489.728
• Mol file: 155089-08-0.mol

Synonyms:(4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester

Chemical Property of (4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester

There total 5 articles about (4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester 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: 82.0%

lithium benzyloxide (15082-42-5) + [(2E,4E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-methyl-8-oxo-octa-2,4-dienyl]-carbamic acid tert-butyl ester (155089-09-1) → (4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester (155089-08-0)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)60128-4

Reference yield:

((2E,4E)-6-Hydroxy-4-methyl-hexa-2,4-dienyl)-carbamic acid tert-butyl ester → (4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester (155089-08-0)

Guidance literature:

Multi-step reaction with 4 steps

1: DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / -78 °C

2: LDA / tetrahydrofuran / -78 °C

3: 97 percent / imidazole / dimethylformamide / 18 h / 20 °C

4: 82 percent / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60128-4

Reference yield:

((2E,4E)-4-Methyl-6-oxo-hexa-2,4-dienyl)-carbamic acid tert-butyl ester (155089-00-2) → (4E,6E)-(S)-8-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-4,6-dienoic acid benzyl ester (155089-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1: LDA / tetrahydrofuran / -78 °C

2: 97 percent / imidazole / dimethylformamide / 18 h / 20 °C

3: 82 percent / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60128-4

upstream raw materials:

lithium benzyloxide

[(2E,4E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-methyl-8-oxo-octa-2,4-dienyl]-carbamic acid tert-butyl ester

((2E,4E)-4-Methyl-6-oxo-hexa-2,4-dienyl)-carbamic acid tert-butyl ester

(2E,4E)-6-tert-Butoxycarbonylamino-3-methyl-hexa-2,4-dienoic acid ethyl ester