(5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester

Base Information

• Chemical Name: (5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester
• CAS No.: 203052-59-9
• Molecular Formula: C₃₁H₄₂O₃Si
• Molecular Weight: 490.758
• Mol file: 203052-59-9.mol

Synonyms:(5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester

Chemical Property of (5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester

There total 8 articles about (5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic 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: 63.0%

methyl 4-formylbutanoate (6026-86-4) + [(3Z,6Z)-9-(tert-Butyl-diphenyl-silanyloxy)-nona-3,6-dienyl]-triphenyl-phosphonium; iodide → (5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester (203052-59-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(97)10607-4

Reference yield:

5-(tetrahydropyran-2-yloxy)-3-pentyn-1-ol (38996-32-6) → (5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester (203052-59-9)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / Ambient temperature

2: Dowex ion exchange resin / methanol / Ambient temperature

3: 99 percent / CBr₄, Ph₃P / CH₂Cl₂ / 0 °C

4: 75 percent / CuI, nBu₄NI, Na₂CO₃ / dimethylformamide / Ambient temperature

5: 89 percent / H₂, Ni(OAc)2, NaBH₄ / Ambient temperature

6: 1.) MsCl, Et₃N, 2.) NaI / 1.) CH₂Cl₂, RT, 2.) acetone, reflux

7: 99 percent / acetonitrile / Heating

8: 63 percent / n-BuLi, HMPA / tetrahydrofuran / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; carbon tetrabromide; Dowex ion exchange resin; hydrogen; nickel diacetate; tetra-(n-butyl)ammonium iodide; sodium carbonate; methanesulfonyl chloride; triethylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(97)10607-4

Reference yield:

(3Z,5Z)-1-(tert-butyldiphenylsiloxy)nona-3,5-diene-1,9-diol (123167-31-7) → (5Z,8Z,11Z)-14-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-5,8,11-trienoic acid methyl ester (203052-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) MsCl, Et₃N, 2.) NaI / 1.) CH₂Cl₂, RT, 2.) acetone, reflux

2: 99 percent / acetonitrile / Heating

3: 63 percent / n-BuLi, HMPA / tetrahydrofuran / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; methanesulfonyl chloride; triethylamine; sodium iodide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(97)10607-4

upstream raw materials:

methyl 4-formylbutanoate

5-(tetrahydropyran-2-yloxy)-3-pentyn-1-ol

5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol

(3Z,5Z)-1-(tert-butyldiphenylsiloxy)nona-3,5-diene-1,9-diol