(2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Base Information

• Chemical Name: (2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid
• CAS No.: 644989-75-3
• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.45

Synonyms:(2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Chemical Property of (2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

Chemical Property:

Purity/Quality:

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Technology Process of (2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid

There total 4 articles about (2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-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: 90.0%

tert-butyl (2E,7E)-(5S,6R)-5-[(2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoyloxy]-6-methyl-8-phenylocta-2,7-dienoate (644989-74-2) → (2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid (644989-75-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 4h;

DOI:10.1021/jo0302197

Reference yield:

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate (178977-57-6) → (2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid (644989-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

2: 90 percent / TFA / CH₂Cl₂ / 4 h

With dmap; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo0302197

Reference yield:

2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoyl chloride (350245-09-9) → (2E,7E)-(5S,6R)-5-((S)-2-Hydroxy-4-methyl-pentanoyloxy)-6-methyl-8-phenyl-octa-2,7-dienoic acid (644989-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

2: 90 percent / TFA / CH₂Cl₂ / 4 h

With dmap; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo0302197

upstream raw materials:

tert-butyl (2E,7E)-(5S,6R)-5-[(2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoyloxy]-6-methyl-8-phenylocta-2,7-dienoate

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate

2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoyl chloride

Downstream raw materials:

(E)-(3S,10R,16S)-3-Isobutyl-10-(4-methoxy-benzyl)-6,6-dimethyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

(3E)-1-[(2E)-3-(N-{(1R)-2-(3,3-dimethyl-2-oxoazetidin-1-yl)-1-[(4-methoxyphenyl)methyl]-2-oxoethyl}carbamoyl)prop-2-enyl]-(1S,2R)-2-methyl-4-phenylbut-3-enyl (2S)-2-hydroxy-4-methylpentanoate

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