(14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl ester

Base Information

• Chemical Name: (14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl ester
• CAS No.: 479092-56-3
• Molecular Formula: C₄₄H₅₉NO₅Si₂
• Molecular Weight: 738.127

Synonyms:

Chemical Property of (14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl ester

There total 9 articles about (14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl 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:

(3E,5E,7E,9E)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxododeca-3,5,7,9-tetraenoic acid methyl ester (479092-53-0) + (S)-4-(tert-butyldiphenylsilyloxy)-2-triethylsiloxybutanal (479092-55-2) → (14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl ester (479092-56-3)

Guidance literature:

With ethylenediamine diacetic acid; In benzene; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(02)01290-5

Reference yield:

Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate (153011-60-0) → (14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl ester (479092-56-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 3.81 g / imidazole / dimethylformamide / 0 - 20 °C

2: 66 percent / DIBAL / CH₂Cl₂; hexane / -50 - -10 °C

3: 100 percent / SO₃*pyridine; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

4: ethylenediammonium diacetate / benzene / 3 h / 20 °C

With 1H-imidazole; pyridine-SO₃ complex; diisobutylaluminium hydride; dimethyl sulfoxide; ethylenediamine diacetic acid; triethylamine; In hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 4: Knoevenagel condensation;

DOI:10.1016/S0040-4020(02)01290-5

Reference yield:

(3E,5E,7E)-2-[(E)-ethylidene]-4-methyl-9-oxonona-3,5,7-trienoic acid tert-butyl ester (479092-49-4) → (14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-(triethylsiloxy)hexadeca-3,5,7,9,12-pentaenoic acid methyl ester (479092-56-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / 0 °C

1.2: 92 percent / 1,2-dimethoxy-ethane; hexane / 1 h / 20 °C

2.1: BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 98 percent / tetrahydrofuran / 0.17 h / -90 °C

3.1: CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

4.1: 23.5 mg / diethyl ether / 0.17 h / -78 °C

5.1: ethylenediammonium diacetate / benzene / 3 h / 20 °C

With n-butyllithium; ethylenediamine diacetic acid; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; benzene; 1.2: Horner-Emmons reaction / 5.1: Knoevenagel condensation;

DOI:10.1016/S0040-4020(02)01290-5

upstream raw materials:

(3E,5E,7E,9E)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxododeca-3,5,7,9-tetraenoic acid methyl ester

(S)-4-(tert-butyldiphenylsilyloxy)-2-triethylsiloxybutanal

Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate

(3E,5E,7E)-2-[(E)-ethylidene]-4-methyl-9-oxonona-3,5,7-trienoic acid tert-butyl ester

Downstream raw materials:

(12R,13S,14S)-(3E,5E,7E,9E,12E)-16-(tert-butyldiphenylsiloxy)-12-cyano-2-[(E)-ethylidene]-4,10-dimethyl-11-oxo-14-triethylsiloxy-12,13-epoxyhexadeca-3,5,7,9-tetraenoic acid methyl ester

(3E,5E,7E,9E)-11-{(1R,4S,5S)-4-[2-(tert-butyldiphenylsiloxy)ethyl]-2-oxo-3,6-dioxabicyclo[3.1.0]hex-1-yl}-2-[(E)-ethylidene]-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester

(3E,5E,7E,9E)-11-{(2R,3S)-3-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-2-cyano-oxiranyl}-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-undeca-3,5,7,9-tetraenoic acid methyl ester

(3E,5E,7E,9E)-11-{(1R,5S)-4-[2-(tert-butyldiphenylsiloxy)ethyl]-4-hydroxy-2-oxo-3-aza-6-oxabicyclo[3.1.0]hex-1-yl}-2-[(E)-ethylidene]-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester

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