tert-butyl (E)-(1''S,3a''S,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''S,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.:943589-72-8
Molecular Formula:C₂₇H₄₀O₄
Molecular Weight:428.612
Hs Code.:

Synonyms:tert-butyl (E)-(1''S,3a''S,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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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of tert-butyl (E)-(1''S,3a''S,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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of tert-butyl (E)-(1''S,3a''S,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''S,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: 84.0%

: 679788-58-0
tert-butyl (E)-(1''S,3a''S,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

: 943589-72-8
tert-butyl (E)-(1''S,3a''S,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 toluene-4-sulfonic acid; In water; acetone; at 22 ℃; for 12h;
DOI:10.1002/chem.200601240

Reference yield:

: 41878-38-0
(1S,7aS)-1-tert-butoxy-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one

: 943589-72-8
tert-butyl (E)-(1''S,3a''S,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 5 steps

1.1: CuBr₂*SMe₂; tBuLi; DIBALH / HMPT / tetrahydrofuran / 2 h / -100 - -40 °C

1.2: 73 percent / 24 h / -40 - -20 °C

2.1: methyllithium; 4,4'-bipyridyl / tetrahydrofuran / 0.5 h / -15 °C

2.2: 97 percent / tetrahydrofuran / 24 h / -78 - 20 °C

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

3.2: 1.14 g / CuI; LiCl / [Pd₂(dba)3]*CHCl₃ / 1-methyl-pyrrolidin-2-one / 5 h / 65 °C

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

4.2: 90 percent / tri-o-tolylphosphane / trans-di(μ-acetato)bis[o-(di-o-tolylphosphanyl)Bn]diPd(II) / dimethylformamide; acetonitrile; H2O / 4 h / 105 °C

5.1: 84 percent / p-toluenesulfonic acid / acetone; H₂O / 12 h / 22 °C

With 4,4'-bipyridine; copper bromide dimethyl sulfide complex; methyllithium; tert.-butyl lithium; tetrabutylammonium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; acetonitrile; 3.2: Stille coupling / 4.1: Heck reaction;
DOI:10.1002/chem.200601240

Reference yield:

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

: 943589-72-8
tert-butyl (E)-(1''S,3a''S,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: 1.14 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: 90 percent / tri-o-tolylphosphane / trans-di(μ-acetato)bis[o-(di-o-tolylphosphanyl)Bn]diPd(II) / dimethylformamide; acetonitrile; H2O / 4 h / 105 °C

4.1: 84 percent / p-toluenesulfonic acid / acetone; H₂O / 12 h / 22 °C

With tetrabutylammonium acetate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 2.2: Stille coupling / 3.1: Heck reaction;
DOI:10.1002/chem.200601240