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'-(tert-butyldimethylsilanyloxy)-cyclohex-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'-(tert-butyldimethylsilanyloxy)-cyclohex-1'-enyl]acrylate
CAS No.:943589-65-9
Molecular Formula:C₃₃H₅₆O₄Si
Molecular Weight:544.891
Hs Code.:

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'-(tert-butyldimethylsilanyloxy)-cyclohex-1'-enyl]acrylate

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'-(tert-butyldimethylsilanyloxy)-cyclohex-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'-(tert-butyldimethylsilanyloxy)-cyclohex-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'-(tert-butyldimethylsilanyloxy)-cyclohex-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'-(tert-butyldimethylsilanyloxy)-cyclohex-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: 79.0%

: 943589-64-8
(1'S,3a'R,7a'S)-[3-bromo-4-(1'-tert-butoxy-7a'-methyl-2',3',3a',6',7',7a'-hexahydro-1'H-inden-5'-yl)cyclohex-3-enyloxy]-tert-butyldimethylsilane

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 943589-65-9
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'-(tert-butyldimethylsilanyloxy)-cyclohex-1'-enyl]acrylate

Guidance literature:: (1'S,3a'R,7a'S)-[3-bromo-4-(1'-tert-butoxy-7a'-methyl-2',3',3a',6',7',7a'-hexahydro-1'H-inden-5'-yl)cyclohex-3-enyloxy]-tert-butyldimethylsilane; tert-Butyl acrylate; With tetrabutylammonium acetate; In water; N,N-dimethyl-formamide; acetonitrile; for 0.0833333h; sonification;

With tris-(o-tolyl)phosphine; trans-di(μ-acetato)bis[o-(di-o-tolylphosphanyl)Bn]diPd(II); In water; N,N-dimethyl-formamide; acetonitrile; at 105 ℃; for 4h; Further stages.;
DOI:10.1002/chem.200601240

Reference yield:

: 943589-86-4
2-bromo-4-(tert-butyldimethylsilyloxy)cyclohexanone

: 943589-65-9
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'-(tert-butyldimethylsilanyloxy)-cyclohex-1'-enyl]acrylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / potassium hexamethyldisilazide / diethyl ether; toluene / 20 h / -78 - 20 °C

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

2.2: 1.18 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: 79 percent / tri-o-tolylphosphane / trans-di(μ-acetato)bis[o-(di-o-tolylphosphanyl)Bn]diPd(II) / dimethylformamide; acetonitrile; H2O / 4 h / 105 °C

With tetrabutylammonium acetate; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2.2: Stille coupling / 3.1: Heck reaction;
DOI:10.1002/chem.200601240

Reference yield:

: 943589-61-5
(3-bromo-4-trifluoromethanesulfonyloxycyclohex-3-enyloxy)-tert-butyldimethylsilane

: 943589-65-9
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'-(tert-butyldimethylsilanyloxy)-cyclohex-1'-enyl]acrylate

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 1.18 g / CuI; LiCl / [Pd₂(dba)3]*CHCl₃ / 1-methyl-pyrrolidin-2-one / 5 h / 65 °C

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

2.2: 79 percent / tri-o-tolylphosphane / trans-di(μ-acetato)bis[o-(di-o-tolylphosphanyl)Bn]diPd(II) / dimethylformamide; acetonitrile; H2O / 4 h / 105 °C

With tetrabutylammonium acetate; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; 1.2: Stille coupling / 2.1: Heck reaction;
DOI:10.1002/chem.200601240