(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

Base Information

Chemical Name:(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
CAS No.:479092-75-6
Molecular Formula:C₃₈H₄₅NO₇Si
Molecular Weight:655.863
Hs Code.:

(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

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 15 articles about (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 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: 60.0%

: 479092-60-9
(12R,13S,14S)-(3E,5E,7E,9E)-16-(tert-butyldiphenylsiloxy)-12-carbamoyl-4,10-dimethyl-2-[(E)-ethylidene]-12,13-epoxy-14-hydroxy-11-oxohexadeca-3,5,7,9-tetraenoic acid methyl ester

: 479092-75-6
(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

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/S0040-4020(02)01290-5

Reference yield:

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

: 479092-75-6
(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

Guidance literature:: Multi-step reaction with 9 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

7: 51.0 mg / silica gel / ethyl acetate; hexane / 1 h

8: 78 percent / aq. NH₄OH / methanol / 0.33 h / 0 °C

9: 60 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; ammonium hydroxide; n-butyllithium; pyridine-SO₃ complex; ditrityl peroxide; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; ethylenediamine diacetic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene; 4: Knoevenagel condensation / 9: Dess-Martin oxidation;
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

: 479092-75-6
(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

Guidance literature:: Multi-step reaction with 10 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

8.1: 51.0 mg / silica gel / ethyl acetate; hexane / 1 h

9.1: 78 percent / aq. NH₄OH / methanol / 0.33 h / 0 °C

10.1: 60 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

With ammonium hydroxide; n-butyllithium; ditrityl peroxide; silica gel; Dess-Martin periodane; toluene-4-sulfonic acid; ethylenediamine diacetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; ethyl acetate; benzene; 1.2: Horner-Emmons reaction / 5.1: Knoevenagel condensation / 10.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(02)01290-5