7,12-Tetradecadiene-5,9-diynoic acid, 14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-hydroxy-11-methyl-12-(phen ylthio)-, methyl ester, (Z,Z)-

Base Information

• Chemical Name: 7,12-Tetradecadiene-5,9-diynoic acid, 14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-hydroxy-11-methyl-12-(phen ylthio)-, methyl ester, (Z,Z)-
• CAS No.: 138376-08-6
• Molecular Formula: C₂₈H₃₈O₄SSi
• Molecular Weight: 498.759

Synonyms:

Chemical Property of 7,12-Tetradecadiene-5,9-diynoic acid, 14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-hydroxy-11-methyl-12-(phen ylthio)-, methyl ester, (Z,Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7,12-Tetradecadiene-5,9-diynoic acid, 14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-hydroxy-11-methyl-12-(phen ylthio)-, methyl ester, (Z,Z)-

There total 1 articles about 7,12-Tetradecadiene-5,9-diynoic acid, 14-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-hydroxy-11-methyl-12-(phen ylthio)-, methyl ester, (Z,Z)- 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:

(Z)-8-Tributylstannanyl-oct-7-en-5-ynoic acid methyl ester (138376-16-6) + (Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-4-phenylsulfanyl-hex-4-en-1-yn-3-ol (138376-07-5) → (7Z,12Z)-14-(tert-Butyl-dimethyl-silanyloxy)-11-hydroxy-11-methyl-12-phenylsulfanyl-tetradeca-7,12-diene-5,9-diynoic acid methyl ester (138376-08-6)

Guidance literature:

With iodine; N-butylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given. Multistep reaction; 1) CH₂Cl₂, 0 deg C, 2) benzene, 23 deg C;

DOI:10.1016/0040-4039(91)80759-Y

Reference yield:

(7Z,12Z)-14-(tert-Butyl-dimethyl-silanyloxy)-11-hydroxy-11-methyl-12-phenylsulfanyl-tetradeca-7,12-diene-5,9-diynoic acid methyl ester (138376-08-6) → (8Z,13Z)-12-Hydroxy-12-methyl-13-phenylsulfanyl-oxacyclopentadeca-8,13-diene-6,10-diyn-2-one (138376-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1: desilylation

2: hydrolysis

3: DCC, pyridine, PPTS / CHCl₃ / 60 °C

With pyridine; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; In chloroform;

DOI:10.1016/0040-4039(91)80759-Y

Reference yield:

(7Z,12Z)-14-(tert-Butyl-dimethyl-silanyloxy)-11-hydroxy-11-methyl-12-phenylsulfanyl-tetradeca-7,12-diene-5,9-diynoic acid methyl ester (138376-08-6) → (7Z,12Z)-11,14-Dihydroxy-11-methyl-12-phenylsulfanyl-tetradeca-7,12-diene-5,9-diynoic acid methyl ester

Guidance literature:

desilylation;

DOI:10.1016/0040-4039(91)80759-Y

upstream raw materials:

(Z)-8-Tributylstannanyl-oct-7-en-5-ynoic acid methyl ester

(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-4-phenylsulfanyl-hex-4-en-1-yn-3-ol

Downstream raw materials:

(8Z,13Z)-12-Hydroxy-12-methyl-13-phenylsulfanyl-oxacyclopentadeca-8,13-diene-6,10-diyn-2-one

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