tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate

Base Information

Chemical Name:tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate
CAS No.:943589-71-7
Molecular Formula:C₂₇H₄₀O₄
Molecular Weight:428.612
Hs Code.:

Synonyms:tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate

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Chemical Property of tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate

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Technology Process of tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate

There total 10 articles about tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate 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: 61.0%

: 679788-56-8
tert-butyl (E)-(1''S,3a''R,7a''S)-3-[8'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-1',4'-dioxaspiro[4.5]dec-7'-en-7'-yl]acrylate

: 943589-71-7
tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate

Guidance literature:: With pyridinium p-toluenesulfonate; In water; acetone; at 60 ℃; for 12h;
DOI:10.1002/chem.200601240

Reference yield:

: 943589-83-1
7-bromo-1,4-dioxaspiro[4,5]decan-8-one

: 943589-71-7
tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / triethylamine / CH₂Cl₂ / 20 h / -78 - 20 °C

2.1: lithium cyano(bistributylstannyl)cuprate / tetrahydrofuran / 4 h / -78 - 20 °C

2.2: 1.16 g / CuI; LiCl / [Pd₂(dba)3]*CHCl₃ / 1-methyl-pyrrolidin-2-one / 5 h / 65 °C

3.1: nBu₄NOAc / dimethylformamide; acetonitrile; H₂O / 0.08 h / sonification

3.2: 86 percent / tri-o-tolylphosphane / trans-di(μ-acetato)bis[o-(di-o-tolylphosphanyl)Bn]diPd(II) / dimethylformamide; acetonitrile; H2O / 6.5 h / 105 °C

4.1: 61 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 12 h / 60 °C

With tetrabutylammonium acetate; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 2.2: Stille coupling / 3.1: Heck reaction;
DOI:10.1002/chem.200601240

Reference yield:

: 4746-97-8
cyclohexanedione monoethylene ketal

: 943589-71-7
tert-butyl (E)-(1''S,3a''R,7a''S)-3-[2'-(1''-tert-butoxy-7a''-methyl-2'',3'',3a'',6'',7'',7a''-hexahydro-1''H-inden-5''-yl)-5'-oxocyclohex-1'-enyl]acrylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

2.1: 85 percent / N-bromosuccinimide; sodium acetate / tetrahydrofuran; H₂O / 3.5 h / 20 °C

3.1: 90 percent / triethylamine / CH₂Cl₂ / 20 h / -78 - 20 °C

4.1: lithium cyano(bistributylstannyl)cuprate / tetrahydrofuran / 4 h / -78 - 20 °C

4.2: 1.16 g / CuI; LiCl / [Pd₂(dba)3]*CHCl₃ / 1-methyl-pyrrolidin-2-one / 5 h / 65 °C

5.1: nBu₄NOAc / dimethylformamide; acetonitrile; H₂O / 0.08 h / sonification

5.2: 86 percent / tri-o-tolylphosphane / trans-di(μ-acetato)bis[o-(di-o-tolylphosphanyl)Bn]diPd(II) / dimethylformamide; acetonitrile; H2O / 6.5 h / 105 °C

6.1: 61 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 12 h / 60 °C

With N-Bromosuccinimide; sodium acetate; tetrabutylammonium acetate; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 4.2: Stille coupling / 5.1: Heck reaction;
DOI:10.1002/chem.200601240