(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

Base Information

Chemical Name:(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
CAS No.:943589-64-8
Molecular Formula:C₂₆H₄₅BrO₂Si
Molecular Weight:497.632
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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:

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

: 928758-66-1
(+)-(3S,3aS,7aR)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-6-yl trifluoromethanesulfonate

: 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

Guidance literature:: (+)-(3S,3aS,7aR)-3-tert-butoxy-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-6-yl trifluoromethanesulfonate; In tetrahydrofuran; at -78 - 20 ℃; for 4h;

(3-bromo-4-trifluoromethanesulfonyloxycyclohex-3-enyloxy)-tert-butyldimethylsilane; With copper(l) iodide; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 65 ℃; for 5h; Further stages.;
DOI:10.1002/chem.200601240

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 2 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

With potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; toluene; 2.2: Stille coupling;
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

: 943589-64-8
(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

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium; aniline / tetrahydrofuran; liquid ammonia / 2.5 h / -33 °C

1.2: 84 percent / triethylamine / tetrahydrofuran / -78 - 22 °C

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

2.2: 95 percent / tetrahydrofuran / 24 h / -78 - 20 °C

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

3.2: 1.18 g / CuI; LiCl / [Pd₂(dba)3]*CHCl₃ / 1-methyl-pyrrolidin-2-one / 5 h / 65 °C

With 4,4'-bipyridine; methyllithium; lithium; aniline; In tetrahydrofuran; ammonia; 3.2: Stille coupling;
DOI:10.1002/chem.200601240