Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl ester

Base Information

• Chemical Name: Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl ester
• CAS No.: 100311-76-0
• Molecular Formula: C₃₅H₄₂O₄Si
• Molecular Weight: 554.802
• Mol file: 100311-76-0.mol

Synonyms:

Chemical Property of Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl ester

There total 10 articles about Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl 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:

Benzoyl bromide (618-32-6) → Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl ester (100311-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / Et₃N / CH₂Cl₂ / 0 °C

2: aq. TFA / tetrahydrofuran / Ambient temperature

3: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / -78 °C

4: toluene / 3 h / 80 °C

With lead(IV) acetate; sodium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo00356a004

Reference yield:

6-carboxy hexylidene triphenylphosphorane (53036-80-9) → Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl ester (100311-76-0)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / -78 - 20 °C

2: NaHCO₃ / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature

3: 68 percent / AlH₃*Et₂O / tetrahydrofuran / 0.5 h / 0 °C

4: 85 percent / Et₃N / CH₂Cl₂ / 0 °C

5: aq. TFA / tetrahydrofuran / Ambient temperature

6: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / -78 °C

7: toluene / 3 h / 80 °C

With lead(IV) acetate; aluminium hydride * diethyl ether; sodium hydrogencarbonate; sodium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene;

DOI:10.1021/jo00356a004

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3) → Benzoic acid (6Z,10E)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-12-oxo-dodeca-6,10-dienyl ester (100311-76-0)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / -78 - 20 °C

2: NaHCO₃ / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature

3: 68 percent / AlH₃*Et₂O / tetrahydrofuran / 0.5 h / 0 °C

4: 85 percent / Et₃N / CH₂Cl₂ / 0 °C

5: aq. TFA / tetrahydrofuran / Ambient temperature

6: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / -78 °C

7: toluene / 3 h / 80 °C

With lead(IV) acetate; aluminium hydride * diethyl ether; sodium hydrogencarbonate; sodium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene;

DOI:10.1021/jo00356a004

upstream raw materials:

(triphenylphosphoranylidene)acetaldehyde

Benzoic acid (Z)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-10-oxo-dec-6-enyl ester

Benzoyl bromide

6-carboxy hexylidene triphenylphosphorane

Downstream raw materials:

Benzoic acid (6Z,10E,12Z,15Z)-(S)-9-hydroxy-19-methoxycarbonyl-nonadeca-6,10,12,15-tetraenyl ester

Benzoic acid (6Z,10E,12Z,15Z)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-19-methoxycarbonyl-nonadeca-6,10,12,15-tetraenyl ester

Benzoic acid (6Z,10E,12Z,15Z)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-19-carboxy-nonadeca-6,10,12,15-tetraenyl ester

Refernces