8-Tridecenal, 5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,13-bis[(4-methoxyphenyl )methoxy]-2,4,6,8,10,12-hexamethyl-, (2R,3R,4R,5R,6S,8Z,10S,11R,12S)-

Base Information

• Chemical Name: 8-Tridecenal, 5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,13-bis[(4-methoxyphenyl )methoxy]-2,4,6,8,10,12-hexamethyl-, (2R,3R,4R,5R,6S,8Z,10S,11R,12S)-
• CAS No.: 256920-80-6
• Molecular Formula: C47H80O7Si2
• Molecular Weight: 813.319
• Mol file: 256920-80-6.mol

Synonyms:

Chemical Property of 8-Tridecenal, 5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,13-bis[(4-methoxyphenyl )methoxy]-2,4,6,8,10,12-hexamethyl-, (2R,3R,4R,5R,6S,8Z,10S,11R,12S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-Tridecenal, 5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,13-bis[(4-methoxyphenyl )methoxy]-2,4,6,8,10,12-hexamethyl-, (2R,3R,4R,5R,6S,8Z,10S,11R,12S)-

There total 6 articles about 8-Tridecenal, 5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,13-bis[(4-methoxyphenyl )methoxy]-2,4,6,8,10,12-hexamethyl-, (2R,3R,4R,5R,6S,8Z,10S,11R,12S)- 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: 93.0%

(Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-en-1-ol (256920-79-3) → (2E,8Z)-(4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltrideca-2,8-dienal + (Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-enal (256920-80-6)

Guidance literature:

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at -5 - 0 ℃; for 1.5h; Large scale;

DOI:10.1021/op034133r

Reference yield:

(4S,5S)-4-[(Z)-(1R,2R,3S,7S,8R,9S)-2,8-bis(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-1,3,5,7,9-pentamethyldec-5-enyl]-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxane → (2E,8Z)-(4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltrideca-2,8-dienal + (Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-enal (256920-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / toluene / 2 h / -20 - 5 °C / Large scale

2: sulfur trioxide pyridine complex; triethylamine; dimethyl sulfoxide / dichloromethane / 1.5 h / -5 - 0 °C / Large scale

With sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 2: |Parikh-Doering Oxidation;

DOI:10.1021/op034133r

Reference yield:

C32H55BO4Si → (2E,8Z)-(4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-13-(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltrideca-2,8-dienal + (Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-enal (256920-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / N,N-dimethyl-formamide / 22.5 h / 25 °C / Large scale

2: diisobutylaluminium hydride / toluene / 2 h / -20 - 5 °C / Large scale

3: sulfur trioxide pyridine complex; triethylamine; dimethyl sulfoxide / dichloromethane / 1.5 h / -5 - 0 °C / Large scale

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sulfur trioxide pyridine complex; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: |Suzuki Coupling / 3: |Parikh-Doering Oxidation;

DOI:10.1021/op034133r

upstream raw materials:

(Z)-(2S,3S,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-en-1-ol

tert-butyl-((1S,2R)-3-iodo-1-{(R)-1-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-[1,3]dioxin-4-yl]-ethyl}-2-methylpropoxy)dimethylsilane

Downstream raw materials:

1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene

(3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-methoxy-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol

(3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol

(3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-chloro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol