4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester

Base Information

Chemical Name:4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester
CAS No.:886221-14-3
Molecular Formula:C₂₉H₃₇BrO₅
Molecular Weight:545.514
Hs Code.:

Synonyms:4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester

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Chemical Property of 4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester

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Technology Process of 4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester

There total 17 articles about 4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl 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: 95.0%

: 886220-91-3
(E)-1-((1R,2S,3R,4S)-1,3-Dihydroxy-4-methyl-2-vinyl-cyclopentyl)-2,5,5,9-tetramethyl-deca-2,9-diene-1,6-dione

: 586-76-5
4-Bromobenzoic acid

: 886221-14-3
4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 2.5h;
DOI:10.1021/ol060115t

Reference yield:

: 886221-00-7
2,2-dimethyl-4-triethylsilanyloxy-butyraldehyde

: 886221-14-3
4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: Mg / diethyl ether

1.2: 80 percent / diethyl ether / -78 - 20 °C

2.1: 98 percent / imidazole / CH₂Cl₂ / 5 h / 20 °C

3.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 0 °C

4.2: 45 percent / tetrahydrofuran; hexane / 12 h / Heating

5.1: 97 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

6.1: 68 percent / pyridinium p-toluenesulfonate / ethanol / 5 h / 20 °C

7.1: 78 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.67 h / 0 °C

8.1: 99 percent / HF*pyridine / tetrahydrofuran / 1.25 h / 20 °C

9.1: 95 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2.5 h / 0 °C

With pyridine; 1H-imidazole; n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; pyridine hydrogenfluoride; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; 1.2: Grignard addition / 4.2: Horner-Wadsworth-Emmons olefination / 9.1: Mitsunobu reaction;
DOI:10.1021/ol060115t

Reference yield:

: 886220-98-0
2,2-dimethyl-4-triethylsilanyloxy-butyric acid ethyl ester

: 886221-14-3
4-Bromo-benzoic acid (1S,2S,3R,5S)-3-hydroxy-5-methyl-3-((E)-2,5,5,9-tetramethyl-6-oxo-deca-2,9-dienoyl)-2-vinyl-cyclopentyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 1.01 g / Py*SO₃; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 - 20 °C

3.1: Mg / diethyl ether

3.2: 80 percent / diethyl ether / -78 - 20 °C

4.1: 98 percent / imidazole / CH₂Cl₂ / 5 h / 20 °C

5.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 0 °C

6.2: 45 percent / tetrahydrofuran; hexane / 12 h / Heating

7.1: 97 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

8.1: 68 percent / pyridinium p-toluenesulfonate / ethanol / 5 h / 20 °C

9.1: 78 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.67 h / 0 °C

10.1: 99 percent / HF*pyridine / tetrahydrofuran / 1.25 h / 20 °C

11.1: 95 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2.5 h / 0 °C

With pyridine; 1H-imidazole; n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; 3.2: Grignard addition / 6.2: Horner-Wadsworth-Emmons olefination / 11.1: Mitsunobu reaction;
DOI:10.1021/ol060115t