(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

Base Information

Chemical Name:(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
CAS No.:1053709-51-5
Molecular Formula:C₃₈H₄₅NO₆Si
Molecular Weight:639.864
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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:

: 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

: 1053709-51-5
(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

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 0 - 20 ℃;
DOI:10.1016/S0040-4020(02)01290-5

Reference yield:

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

: 1053709-51-5
(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

Guidance literature:: Multi-step reaction with 6 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

6: TsOH*H₂O / tetrahydrofuran; H₂O / 0 - 20 °C

With 1H-imidazole; n-butyllithium; pyridine-SO₃ complex; ditrityl peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; ethylenediamine diacetic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; 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

: 1053709-51-5
(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

Guidance literature:: Multi-step reaction with 7 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

7.1: TsOH*H₂O / tetrahydrofuran; H₂O / 0 - 20 °C

With n-butyllithium; ditrityl peroxide; toluene-4-sulfonic acid; ethylenediamine diacetic acid; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; benzene; 1.2: Horner-Emmons reaction / 5.1: Knoevenagel condensation;
DOI:10.1016/S0040-4020(02)01290-5