2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

Base Information

Chemical Name:2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester
CAS No.:916757-58-9
Molecular Formula:C₅₅H₉₅BrO₈Si₄
Molecular Weight:1076.6
Hs Code.:

2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

Synonyms:2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

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Chemical Property of 2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

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Technology Process of 2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

There total 39 articles about 2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl 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: 93.0%

: 916757-45-4
2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid

: 916757-57-8
2,6,10,12-tetrakis-(tert-butyl-dimethyl-silanyloxy)-14-methyl-heptadeca-8,14-dien-16-yn-4-ol

: 916757-58-9
2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 25 ℃; for 1h;
DOI:10.1002/anie.200601867 DOI:10.1021/ja068053p

Reference yield:

: 931416-77-2
2,2-dimethyl-5-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-benzo[1,3]dioxin-4-one

: 916757-58-9
2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / aq. Cs₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 55 °C

2: 88 percent / N-bromosuccinimide / acetonitrile / 0.25 h / 25 °C

3: 87 percent / aq. KOH / tetrahydrofuran / 18 h / 55 °C

4: 96 percent / Mg(ClO₄)2 / 48 h / 25 °C

5: 93 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran / 1 h / 25 °C

With potassium hydroxide; N-Bromosuccinimide; magnesium(II) perchlorate; caesium carbonate; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; acetonitrile; 5: Mitsunobu reaction;
DOI:10.1021/ja068053p

Reference yield:

: 71171-66-9,92775-37-6,116839-04-4,72150-39-1
(3R)-3-(tert-butyldimethylsilyloxy)butanal

: 916757-58-9
2-acetoxy-6-(4-bromo-buta-1,3-dienyl)-benzoic acid 3,7,9-tris-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-11-methyl-tetradeca-5,11-dien-13-ynyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 20.5 g / diethyl ether / 5 h / -78 - 25 °C

2.1: 28.3 g / imidazole / dimethylformamide / 4 h / 25 °C

3.1: O₃ / CH₂Cl₂ / 4 h / -78 °C

3.2: 64 percent / PPh₃ / diethyl ether / 3 h / -78 - 25 °C

4.1: 18.5 g / diethyl ether / 5 h / -78 - 25 °C

5.1: imidazole / dimethylformamide / 4 h / 25 °C

6.1: 36 percent / Hoveyda-Grubbs' catalyst / CH₂Cl₂ / 18 h / 25 °C

7.1: Et₂BOMe / tetrahydrofuran; methanol / 0.25 h / -78 °C

7.2: 89 percent / NaBH₄ / tetrahydrofuran; methanol; various solvent(s) / 3 h / -78 °C

8.1: 89 percent / imidazole / dimethylformamide / 8 h / 25 °C

9.1: 75 percent / liquid NH₃; calcium / tetrahydrofuran; propan-2-ol / 1 h / -78 °C

10.1: 87 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

11.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C

11.2: 85 percent / tetrahydrofuran; hexane; toluene / 3 h / -78 - 25 °C

12.1: 77 percent / pyridinium p-toluenesulfonate / ethanol / 3 h / 25 °C

13.1: 93 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran / 1 h / 25 °C

With 1H-imidazole; n-butyllithium; diethyl methoxy borane; ammonia; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; calcium; Dess-Martin periodane; ozone; diisopropylamine; triphenylphosphine; diethylazodicarboxylate; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 13.1: Mitsunobu reaction;
DOI:10.1021/ja068053p