(5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ⁵-phosphanylidene)-undeca-5,9-dienoic acid methyl ester

Base Information

• Chemical Name: (5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ⁵-phosphanylidene)-undeca-5,9-dienoic acid methyl ester
• CAS No.: 100572-54-1
• Molecular Formula: C₃₈H₅₁O₃PSi
• Molecular Weight: 614.88
• Mol file: 100572-54-1.mol

Synonyms:

Chemical Property of (5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ⁵-phosphanylidene)-undeca-5,9-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ⁵-phosphanylidene)-undeca-5,9-dienoic acid methyl ester

There total 1 articles about (5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ⁵-phosphanylidene)-undeca-5,9-dienoic acid methyl 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:

<(4E,8E)-5,9-dimethyl-10-<(tert-butyldimethylsilyl)oxy>-4,8-decadienyl>triphenylphosphonium iodide (100572-53-0) + methyl chloroformate (79-22-1) → (5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ5-phosphanylidene)-undeca-5,9-dienoic acid methyl ester (100572-54-1)

Guidance literature:

With potassium hexamethylsilazane; Multistep reaction; 1.) THF, toluene, -78 deg C, 1.5 h, 2.) THF, toluene, from -78 deg C to RT, 2 h;

DOI:10.1021/jo00356a021

Reference yield:

(5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ5-phosphanylidene)-undeca-5,9-dienoic acid methyl ester (100572-54-1) → rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol (100572-58-5)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; toluene / 32 h

2: 94 percent / i-Bu₂AlH / tetrahydrofuran; CH₂Cl₂ / 0.67 h / -78 °C

3: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, -78 deg C, 2.) THF, HMPA, from -78 deg C to RT,

4: tetra-n-butylammonium fluoride / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 25 °C

With n-butyllithium; 1,10-Phenanthroline; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene;

DOI:10.1021/jo00356a021

Reference yield:

(5E,9E)-11-(tert-Butyl-dimethyl-silanyloxy)-6,10-dimethyl-2-(triphenyl-λ5-phosphanylidene)-undeca-5,9-dienoic acid methyl ester (100572-54-1) → C40H49IO4S (100572-60-9)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran; toluene / 32 h

2: 94 percent / i-Bu₂AlH / tetrahydrofuran; CH₂Cl₂ / 0.67 h / -78 °C

3: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, -78 deg C, 2.) THF, HMPA, from -78 deg C to RT,

4: tetra-n-butylammonium fluoride / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 25 °C

5: PPh₃, imidazole, I₂ / acetonitrile; diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; n-butyllithium; 1,10-Phenanthroline; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo00356a021

upstream raw materials:

<(4E,8E)-5,9-dimethyl-10-<(tert-butyldimethylsilyl)oxy>-4,8-decadienyl>triphenylphosphonium iodide

methyl chloroformate

Downstream raw materials:

rel-(2S,3R)-(4E,8E,12E)-2-isopropenyl-3-(benzyloxy)-5-carbomethoxy-9,13-dimethyl-14-<(tert-butyldimethylsilyl)oxy>-4,8,12-tetradecatrienyl phenyl sulfone

rel-(1R,2S)-(3E,7E,11E)-1-isopropenyl-4-<(benzoyloxy)methyl>-8,12-dimethyl-3,7,11-cyclotetradecatrien-2-ol

rel-(2S,3R)-(4E,8E,12E)-2-isopropenyl-3-(benzyloxy)-5-(hydroxymethyl)-9,13-dimethyl-14-<(tert-butyldimethylsilyl)oxy>-4,8,12-tetradecatrienyl phenyl sulfone

rel-(1R,2S)-(3E,7E,11E)-1-isopropenyl-2-(benzyloxy)-4-<(benzyloxy)methyl>-8,12-dimethyl-14-(phenylsulfonyl)-3,7,11-cyclotetradecatriene