(6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester

Base Information

• Chemical Name: (6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester
• CAS No.: 1027166-75-1
• Molecular Formula: C₃₈H₆₂O₅Si₃
• Molecular Weight: 683.164

Synonyms:(6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester

Chemical Property of (6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester

There total 6 articles about (6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl 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:

(2E,5Z)-7-(tert-butyldiphenylsilanyloxy)-5-methylhepta-2,5-dienal (860651-93-0) → (6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester (1027166-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1: SiCl₄; chiral Denmark's bisphosphoramide catalyst / CH₂Cl₂ / 18 h / -78 °C

2: 1 h / Heating

3: diethylmethoxyborane; NaBH₄ / tetrahydrofuran / 18 h / -78 °C

4: imidazole; 4-dimethylaminopyridine / dimethylformamide / 18 h

With 1H-imidazole; dmap; sodium tetrahydroborate; tetrachlorosilane; chiral Denmark's bisphosphoramide catalyst; diethyl methoxy borane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200500564

Reference yield:

tert-Butyl-((2Z,5E)-7,7-dimethoxy-3-methyl-hepta-2,5-dienyloxy)-diphenyl-silane → (6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester (1027166-75-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.95 g / HCO₂H / CH₂Cl₂; CHCl₃ / 1 h / 20 °C

2: SiCl₄; chiral Denmark's bisphosphoramide catalyst / CH₂Cl₂ / 18 h / -78 °C

3: 1 h / Heating

4: diethylmethoxyborane; NaBH₄ / tetrahydrofuran / 18 h / -78 °C

5: imidazole; 4-dimethylaminopyridine / dimethylformamide / 18 h

With 1H-imidazole; dmap; sodium tetrahydroborate; formic acid; tetrachlorosilane; chiral Denmark's bisphosphoramide catalyst; diethyl methoxy borane; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1002/anie.200500564

Reference yield:

6-[(S,3E,6Z)-8-(tert-butyldiphenylsilanyloxy)-2-hydroxy-6-methylocta-3,6-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one (860651-95-2) → (6E,9Z)-(3R,5S)-11-(tert-Butyl-diphenyl-silanyloxy)-9-methyl-3,5-bis-trimethylsilanyloxy-undeca-6,9-dienoic acid butyl ester (1027166-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1 h / Heating

2: diethylmethoxyborane; NaBH₄ / tetrahydrofuran / 18 h / -78 °C

3: imidazole; 4-dimethylaminopyridine / dimethylformamide / 18 h

With 1H-imidazole; dmap; sodium tetrahydroborate; diethyl methoxy borane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/anie.200500564

upstream raw materials:

(3R,5S,6E,9Z)-11-(tert-butyldiphenylsilanyloxy)-3,5-dihydroxy-9-methylundeca-6,9-dienoic acid butyl ester

chloro-trimethyl-silane

(2E,5Z)-7-(tert-butyldiphenylsilanyloxy)-5-methylhepta-2,5-dienal

6-[(S,3E,6Z)-8-(tert-butyldiphenylsilanyloxy)-2-hydroxy-6-methylocta-3,6-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one

Downstream raw materials:

(2R,6S)-2-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-pent-1-enyl]-6-[(3E,6Z)-(S)-8-(tert-butyl-diphenyl-silanyloxy)-6-methyl-2-phenylselanyl-octa-3,6-dienyl]-4-methylene-tetrahydro-pyran

(2S,3E,6Z)-1-((2S,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-3,6-dien-2-ol

(2E,4S,6Z)-1-((2R,6R)-{6-(R,E)-[4-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2-methylpent-1-enyl]-4-methylenetetrahydropyran-2-yl})-8-(tert-butyldiphenylsilanyloxy)-6-methylocta-2,6-dien-4-ol

(diethoxyphosphoryl)acetic acid (R)-4-((2R,6R)-{6-((2E,4S,6Z)-[4-(4-methoxybenzyloxymethoxy)-6-methyl-8-oxoocta-2,6-dienyl])-4-methylenetetrahydropyran-2-yl})-1-(4-methoxybenzyloxymethyl)-[(E)-3-methylbut-3-en]yl ester

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