(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

Base Information

Chemical Name:(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
CAS No.:1054654-78-2
Molecular Formula:C₄₄H₅₉NO₆Si₂
Molecular Weight:754.127
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 11 articles about (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 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:

: 479092-56-3
(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

: 1054654-78-2
(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

Guidance literature:: With n-butyllithium; ditrityl peroxide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1016/S0040-4020(02)01290-5

Reference yield:

: 153011-60-0
Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate

: 1054654-78-2
(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

Guidance literature:: Multi-step reaction with 5 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

5: trityl peroxide; BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; n-butyllithium; pyridine-SO₃ complex; ditrityl peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; ethylenediamine diacetic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 4: Knoevenagel condensation;
DOI:10.1016/S0040-4020(02)01290-5

Reference yield:

: 479092-49-4
(3E,5E,7E)-2-[(E)-ethylidene]-4-methyl-9-oxonona-3,5,7-trienoic acid tert-butyl ester

: 1054654-78-2
(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

Guidance literature:: Multi-step reaction with 6 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

6.1: trityl peroxide; BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

With n-butyllithium; ditrityl peroxide; 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