1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

Base Information

Chemical Name:1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester
CAS No.:251980-61-7
Molecular Formula:C₃₆H₆₀BrF₃O₄SSi
Molecular Weight:753.921
Hs Code.:

1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

Synonyms:1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

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Chemical Property of 1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

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Technology Process of 1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

There total 8 articles about 1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester 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:

: 2979-19-3
3,3-dimethylcyclohexanone

: 251980-61-7
1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: PBr₃ / CHCl₃ / 0.5 h / 70 °C

1.2: CHCl₃ / 1.5 h / 70 °C

2.1: DIBAL / diethyl ether; toluene / 1 h / 23 °C

3.1: Et₃N / tetrahydrofuran / 0.5 h / -40 °C

4.1: 92 percent / LiBr / tetrahydrofuran / 1 h / 0 °C

5.1: 84 percent

6.1: MeAlCl₂ / hexane; CH₂Cl₂ / 0.5 h / -78 °C

7.1: imidazole / CH₂Cl₂ / 20 h / Heating

8.1: LDA / tetrahydrofuran / 1.5 h / -78 - 0 °C

8.2: 84 percent / tetrahydrofuran / 2 h / -78 - 23 °C

With 1H-imidazole; methylaluminum dichloride; phosphorus tribromide; diisobutylaluminium hydride; triethylamine; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; toluene; 1.1: phosphorylation / 1.2: Formylation / 2.1: Reduction / 3.1: mesylation / 4.1: Bromination / 6.1: Cyclization / 7.1: silylation / 8.1: deprotonation / 8.2: triflation;
DOI:10.1021/ja992411p

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 251980-61-7
1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: imidazole / CH₂Cl₂ / 20 h / Heating

2.1: LDA / tetrahydrofuran / 1.5 h / -78 - 0 °C

2.2: 84 percent / tetrahydrofuran / 2 h / -78 - 23 °C

With 1H-imidazole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1.1: silylation / 2.1: deprotonation / 2.2: triflation;
DOI:10.1021/ja992411p

Reference yield:

: 251980-67-3
2-bromo-4,4-dimethylcyclohex-1-ene-1-carbaldehyde

: 251980-61-7
1,1,1-trifluoromethanesulfonic acid (1S,4aR,4bR,7S,8aR,10aR)-1-[2-(2-bromo-4,4-dimethylcyclohex-1-enyl)ethyl]-7-tert-butyldimethylsiloxy-1,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-2-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: DIBAL / diethyl ether; toluene / 1 h / 23 °C

2.1: Et₃N / tetrahydrofuran / 0.5 h / -40 °C

3.1: 92 percent / LiBr / tetrahydrofuran / 1 h / 0 °C

4.1: 84 percent

5.1: MeAlCl₂ / hexane; CH₂Cl₂ / 0.5 h / -78 °C

6.1: imidazole / CH₂Cl₂ / 20 h / Heating

7.1: LDA / tetrahydrofuran / 1.5 h / -78 - 0 °C

7.2: 84 percent / tetrahydrofuran / 2 h / -78 - 23 °C

With 1H-imidazole; methylaluminum dichloride; diisobutylaluminium hydride; triethylamine; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1.1: Reduction / 2.1: mesylation / 3.1: Bromination / 5.1: Cyclization / 6.1: silylation / 7.1: deprotonation / 7.2: triflation;
DOI:10.1021/ja992411p