Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester
• CAS No.: 284480-96-2
• Molecular Formula: C₃₂H₄₈O₆SSi
• Molecular Weight: 588.881

Synonyms:Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester

Chemical Property of Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester

There total 12 articles about Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-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: 92.0%

t-butyldimethylsiyl triflate (69739-34-0) + Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-hydroxy-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester (284480-94-0) → Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester (284480-96-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)00412-3

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester (284480-96-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 95 percent / CSA / CH₂Cl₂ / 36 h / 20 °C

2.1: 99 percent / DIBAL-H / toluene / 0.5 h / 0 °C

3.1: 90 percent / I₂; Ph₃P; imidazole / toluene / 1 h / 20 °C

4.1: 84 percent / nBu₄NBr / dimethylformamide / 2 h / 40 °C

5.1: LiHDMS / tetrahydrofuran / 0.25 h / -78 °C

5.2: tetrahydrofuran / 0.25 h / -78 °C

6.1: 68 percent / Na(Hg)(6 percent); Na₂HPO₄ / methanol / 0.5 h / 0 °C

7.1: 83 percent / CSA; MeOH / 3 h / 20 °C

8.1: 69 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

9.1: 92 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

With 1H-imidazole; methanol; disodium hydrogenphosphate; sodium amalgam; camphor-10-sulfonic acid; tetrabutylammomium bromide; iodine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Reduction / 3.1: Iodination / 4.1: Substitution / 5.1: Metallation / 5.2: Substitution / 6.1: Reduction / 7.1: methanolysis / 8.1: Tosylation / 9.1: Substitution;

DOI:10.1016/S0040-4039(00)00412-3

Reference yield:

(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate (185030-60-8) → Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester (284480-96-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / DIBAL-H / toluene / 0.5 h / 0 °C

2.1: 90 percent / I₂; Ph₃P; imidazole / toluene / 1 h / 20 °C

3.1: 84 percent / nBu₄NBr / dimethylformamide / 2 h / 40 °C

4.1: LiHDMS / tetrahydrofuran / 0.25 h / -78 °C

4.2: tetrahydrofuran / 0.25 h / -78 °C

5.1: 68 percent / Na(Hg)(6 percent); Na₂HPO₄ / methanol / 0.5 h / 0 °C

6.1: 83 percent / CSA; MeOH / 3 h / 20 °C

7.1: 69 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

8.1: 92 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

With 1H-imidazole; methanol; disodium hydrogenphosphate; sodium amalgam; camphor-10-sulfonic acid; tetrabutylammomium bromide; iodine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Reduction / 2.1: Iodination / 3.1: Substitution / 4.1: Metallation / 4.2: Substitution / 5.1: Reduction / 6.1: methanolysis / 7.1: Tosylation / 8.1: Substitution;

DOI:10.1016/S0040-4039(00)00412-3

upstream raw materials:

t-butyldimethylsiyl triflate

Toluene-4-sulfonic acid (3E,5E)-(2S,10R)-2-hydroxy-10-(4-methoxy-benzyloxy)-undeca-3,5-dienyl ester

O-(4-methoxybenzyl)-trichloroacetimidate

(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate

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