(E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

Base Information

Chemical Name:(E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one
CAS No.:1287695-75-3
Molecular Formula:C₄₁H₅₈O₄Si₂
Molecular Weight:671.08
Hs Code.:

Synonyms:(E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

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Chemical Property of (E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

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Technology Process of (E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

There total 6 articles about (E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one 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: 83.0%

: 1287695-73-1
(((1R,2S)-2-allyl-3-(5-(4-(tert-butyldiphenylsiloxy)butyl)furan-2-yl)-2-methyl-cyclopent-3-en-1-yl)oxy)(tert-butyl)dimethylsilane

: 78-94-4,25038-87-3
methyl vinyl ketone

: 1287695-75-3
(E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1039/c1cc00087j

Reference yield:

: 1287695-82-2
(2R,3R)-2-allyl-3-(tert-butyldimethylsiloxy)-2-methylcyclopentanone

: 1287695-75-3
(E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 0 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 °C / Inert atmosphere

With n-butyllithium; Hoveyda-Grubbs catalyst second generation; N,N,N,N,-tetramethylethylenediamine; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1039/c1cc00087j

Reference yield:

: 26828-48-8
2-allyl-2-methyl-1,3-cyclopentanedione

: 1287695-75-3
(E)-5-((1S,5R)-5-(tert-butyldimethylsilyloxy)-2-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-1-methylcyclopent-2-en-1-yl)pent-3-en-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,N-diethylaniline; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 2 h / -78 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 0 °C / Inert atmosphere

3.2: 3 h / -78 °C / Inert atmosphere

4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; Hoveyda-Grubbs catalyst second generation; N,N,N,N,-tetramethylethylenediamine; methanesulfonyl chloride; triethylamine; N,N-diethylaniline; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/c1cc00087j