2,4,6,10,12-Pentadecapentaenoic acid, 6,12-dibromo-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,8-trimethyl-15- phenyl-, 2-(trimethylsilyl)ethyl ester, (2E,4E,6Z,8R,9R,10E,12Z)-

Base Information

Chemical Name:2,4,6,10,12-Pentadecapentaenoic acid, 6,12-dibromo-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,8-trimethyl-15- phenyl-, 2-(trimethylsilyl)ethyl ester, (2E,4E,6Z,8R,9R,10E,12Z)-
CAS No.:836671-19-3
Molecular Formula:C35H54Br2O3Si2
Molecular Weight:738.791
Hs Code.:

2,4,6,10,12-Pentadecapentaenoic acid,
6,12-dibromo-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,8-trimethyl-15-
phenyl-, 2-(trimethylsilyl)ethyl ester, (2E,4E,6Z,8R,9R,10E,12Z)-

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Chemical Property of 2,4,6,10,12-Pentadecapentaenoic acid, 6,12-dibromo-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,8-trimethyl-15- phenyl-, 2-(trimethylsilyl)ethyl ester, (2E,4E,6Z,8R,9R,10E,12Z)-

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Technology Process of 2,4,6,10,12-Pentadecapentaenoic acid, 6,12-dibromo-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,8-trimethyl-15- phenyl-, 2-(trimethylsilyl)ethyl ester, (2E,4E,6Z,8R,9R,10E,12Z)-

There total 9 articles about 2,4,6,10,12-Pentadecapentaenoic acid, 6,12-dibromo-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,4,8-trimethyl-15- phenyl-, 2-(trimethylsilyl)ethyl ester, (2E,4E,6Z,8R,9R,10E,12Z)- 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: 36.0%

: 836671-16-0
2,4-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-penta-2,4-dienoic acid 2-trimethylsilanylethyl ester

: 836671-18-2
[4-bromo-1-(3,3-dibromo-1-methyl-allyl)-7-phenyl-hepta-2,4-dienyloxy]-tert-butyl-dimethyl-silane

: 836671-19-3
6,12-dibromo-9-(tert-butyldimethyl-silanyloxy)-2,4,8-trimethyl-15-phenyl-pentadeca-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; thallium (I) ethoxide; In tetrahydrofuran; water; for 0.5h;
DOI:10.1016/j.tet.2004.10.088

Reference yield:

: 836671-15-9
5-iodo-2,4-dimethyl-penta-2,4-dienoic acid 2-trimethylsilanyl-ethyl ester

: 836671-19-3
6,12-dibromo-9-(tert-butyldimethyl-silanyloxy)-2,4,8-trimethyl-15-phenyl-pentadeca-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / PdCl₂(dppf); KOAc / dimethylsulfoxide; CH₂Cl₂ / 0.17 h / 80 °C

2: 36 percent / Pd(PPh₃)4; TlOEt / tetrahydrofuran; H₂O / 0.5 h

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; thallium (I) ethoxide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 2: Suzuki coupling;
DOI:10.1016/j.tet.2004.10.088

Reference yield:

: 836671-07-9
3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-enal

: 836671-19-3
6,12-dibromo-9-(tert-butyldimethyl-silanyloxy)-2,4,8-trimethyl-15-phenyl-pentadeca-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 70 percent / Pd(PPh₃)4; TlOEt / tetrahydrofuran; H₂O / 2.5 h

2.1: PPh₃; t-BuOK / tetrahydrofuran / 0.33 h / 20 °C

2.2: 77 percent / tetrahydrofuran / 15 h / 0 °C

3.1: 36 percent / Pd(PPh₃)4; TlOEt / tetrahydrofuran; H₂O / 0.5 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; thallium (I) ethoxide; triphenylphosphine; In tetrahydrofuran; water; 1.1: Suzuki coupling / 3.1: Suzuki coupling;
DOI:10.1016/j.tet.2004.10.088