(2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid

Base Information

Chemical Name:(2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid
CAS No.:281190-94-1
Molecular Formula:C₂₄H₃₈O₃Si
Molecular Weight:402.649
Hs Code.:

Synonyms:(2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid

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Chemical Property of (2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid

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Technology Process of (2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid

There total 10 articles about (2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid 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: 94.0%

: 281191-00-2
(2E,5S,6R,7E)-ethyl 6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoate

: 281190-94-1
(2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid

Guidance literature:: With lithium hydroxide; In ethanol; water; at 20 ℃; for 2h;
DOI:10.1002/ejoc.200300814

Reference yield: 33.0%

: 141-82-2
malonic acid

: 281191-05-7
(3S,4R,5E)-4-methyl-6-phenyl-3-[(triisopropylsilanyl)oxy]hex-5-enal

: 281190-94-1
(2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid

Guidance literature:: With triethylamine; In benzene; for 4h; Heating;
DOI:10.1002/ejoc.200300814

Reference yield:

: 2243-53-0,59744-46-6,1914-58-5
trans-styrylacetic acid

: 281190-94-1
(2E,5S,6R,7E)-6-methyl-8-phenyl-5-[(triisopropylsilanyl)oxy]octa-2,7-dienoic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: DMAP / CH₂Cl₂ / 1 h / 20 °C

1.2: 98 percent / EDCI / CH₂Cl₂ / 6 h / 20 °C

2.1: TiCl₄; iPrNEt / CH₂Cl₂ / 1 h / 20 °C

2.2: 98 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

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

4.1: phenyllithium; TsCl / tetrahydrofuran; cyclohexane; diethyl ether / 0.5 h / -78 - -20 °C

4.2: 96 percent / LAH / tetrahydrofuran; diethyl ether; cyclohexane / 0.33 h / -20 °C

5.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 20 h / 20 °C

6.1: 83 percent / K₂CO₃; BBr₃ / CH₂Cl₂ / 0.08 h / 0 °C

7.1: 98 percent / molecular sieves (4 Angstroem); PCC / CH₂Cl₂ / 0.17 h / 20 °C

8.1: 92 percent / NaH / tetrahydrofuran / 0.17 h / 0 °C

9.1: 94 percent / LiOH*H₂O / ethanol; H₂O / 2 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; boron tribromide; titanium tetrachloride; sodium hydride; potassium carbonate; N-isopropylethylamine; phenyllithium; p-toluenesulfonyl chloride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; cyclohexane; water; 8.1: Horner-Emmons olefination;
DOI:10.1002/ejoc.200300814