(2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester

Base Information

• Chemical Name: (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester
• CAS No.: 541551-03-5
• Molecular Formula: C₃₂H₄₄O₄Si
• Molecular Weight: 520.784
• Mol file: 541551-03-5.mol

Synonyms:(2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester

Chemical Property of (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester

There total 5 articles about (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-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: 60.0%

(4-bromophenyl)(phenyl)methanone (90-90-4) + tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate (220249-54-7) → (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester (541551-03-5)

Guidance literature:

With palladium diacetate; tetrabutylammomium bromide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 85 ℃; for 12h;

DOI:10.1016/S0960-894X(02)01023-5

Reference yield:

(3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhex-5-en-1-ol (311341-98-7) → (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester (541551-03-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess-Martin periodinane

2: 95 percent / CH₂Cl₂

3: 60 percent / NaHCO₃; Pd(OAc)2; Bu₄NBr / dimethylformamide / 12 h / 85 °C

With palladium diacetate; tetrabutylammomium bromide; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide; 2: Wittig-Horner olefination / 3: Heck coupling;

DOI:10.1016/S0960-894X(02)01023-5

Reference yield:

(3S,4R)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-5-hexenal (220249-57-0) → (2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester (541551-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / CH₂Cl₂

2: 60 percent / NaHCO₃; Pd(OAc)2; Bu₄NBr / dimethylformamide / 12 h / 85 °C

With palladium diacetate; tetrabutylammomium bromide; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide; 1: Wittig-Horner olefination / 2: Heck coupling;

DOI:10.1016/S0960-894X(02)01023-5

upstream raw materials:

(4-bromophenyl)(phenyl)methanone

tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate

(3S,4R)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-5-hexenal

(3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhex-5-en-1-ol

Downstream raw materials:

(2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-hydroxy-6-methyl-octa-2,7-dienoic acid tert-butyl ester

(E)-(3S,10R,16S)-16-[(E)-(R)-3-(4-Benzoyl-phenyl)-1-methyl-allyl]-3-isobutyl-10-(4-methoxy-benzyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

(2E,7E)-(5S,6R)-8-(4-Benzoyl-phenyl)-5-((S)-2-{3-[(R)-2-tert-butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoyloxy)-6-methyl-octa-2,7-dienoic acid tert-butyl ester