(1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane

Base Information

Chemical Name:(1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane
CAS No.:1027425-65-5
Molecular Formula:C₃₉H₇₈O₃Si₃
Molecular Weight:679.303
Hs Code.:

Synonyms:(1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane

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Chemical Property of (1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane

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Technology Process of (1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane

There total 12 articles about (1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane 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:

: 387834-47-1
(R)-(E)-2-[6,10-dimethyl-10-(triethylsilanyloxy)undec-1-enyl]-5,5-dimethyl[1,3,2]dioxaborolane

: 502495-26-3
(Z)-(3S,5R)-1-bromomethylene-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexane

: 1027425-65-5
(1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; at 40 ℃;
DOI:10.1021/ol0274007

Reference yield:

: 161055-33-0
(S,E)-5-(tert-butyldimethylsilyloxy)-8-(trimethylsilyl)oct-2-en-7-yn-1-ol

: 1027425-65-5
(1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane

Guidance literature:: Multi-step reaction with 9 steps

1.1: diisopropyl (L)-(+)-tartrate; Ti(O-i-Pr)4; t-BuOOH / CH₂Cl₂ / 24 h / -20 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

3.1: NaI; NaHCO₃ / acetone / 20 h / 20 °C

4.1: 21.7 g / Zn; AcOH / methanol / 1 h / sonication

5.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C

5.2: 51 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C

6.1: 96 percent / imidazole / dimethylformamide / 12 h / 20 °C

7.1: DBU / toluene / 20 h / 70 °C

8.1: 1.16 g / Cs₂CO₃ / dimethylformamide / 12 h / 20 °C

9.1: aq. KOH; PdCl₂(dppf) / tetrahydrofuran / 60 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; diisopropyl (L)-tartrate; isopropylmagnesium chloride; sodium hydrogencarbonate; caesium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Sharpless asymmetric epoxidation / 9.1: Suzuki-Miyaura coupling;
DOI:10.1021/jo0353435

Reference yield:

: 143724-89-4
Trimethyl-((R)-3-oxiranyl-prop-1-ynyl)-silane

: 1027425-65-5
(1S,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-(R)-7,11-dimethyl-11-triethylsilanyloxy-dodec-2-en-(Z)-ylidene]-2-methylene-cyclohexane

Guidance literature:: Multi-step reaction with 13 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: BF₃*Et₂O / tetrahydrofuran; hexane / -78 - 20 °C

1.3: 82 percent / hydrochloric acid / tetrahydrofuran / 1 h / 20 °C

2.1: 96 percent / porcine pancreatic lipase / 72 h / 20 °C

3.1: imidazole / dimethylformamide / 12 h / 20 °C

4.1: 27.8 g / Red-Al / diethyl ether; toluene / 1 h / 0 °C

5.1: diisopropyl (L)-(+)-tartrate; Ti(O-i-Pr)4; t-BuOOH / CH₂Cl₂ / 24 h / -20 °C

6.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

7.1: NaI; NaHCO₃ / acetone / 20 h / 20 °C

8.1: 21.7 g / Zn; AcOH / methanol / 1 h / sonication

9.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C

9.2: 51 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C

10.1: 96 percent / imidazole / dimethylformamide / 12 h / 20 °C

11.1: DBU / toluene / 20 h / 70 °C

12.1: 1.16 g / Cs₂CO₃ / dimethylformamide / 12 h / 20 °C

13.1: aq. KOH; PdCl₂(dppf) / tetrahydrofuran / 60 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; n-butyllithium; porcine pancreatic lipase; diisopropyl (L)-tartrate; isopropylmagnesium chloride; sodium hydrogencarbonate; caesium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 5.1: Sharpless asymmetric epoxidation / 13.1: Suzuki-Miyaura coupling;
DOI:10.1021/jo0353435