Technology Process of (2E,5Z)-6-[[2-[(S)-6-hydroxy]heptyl]-1,3-dioxolan-2-yl]-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,5-hexadienoic acid
There total 14 articles about (2E,5Z)-6-[[2-[(S)-6-hydroxy]heptyl]-1,3-dioxolan-2-yl]-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,5-hexadienoic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 4.8 g / pyridinium chlorochromate / CH2Cl2 / 12 h / 25 °C
2.1: HC(OMe)3; TsOH*H2O / benzene / 8 h / Heating
3.1: 3.73 g / K2CO3 / methanol / 12 h / 25 °C
4.1: 99 percent / mCPBA / CH2Cl2 / 12 h / 0 °C
5.1: AcOH / monomeric (salen)Co(II)
5.2: NaBH4 / ethanol / 4 h / 50 °C
6.1: 92 percent / imidazole / dimethylformamide / 12 h / 25 °C
7.1: n-BuLi / hexane; tetrahydrofuran / 12 h / -40 °C
7.2: 74 percent / tetrahydrofuran; hexane / 0.5 h / -40 °C
8.1: 91 percent / H2; quinoline / Pd/CaCO3 (Pb poisoned) / ethyl acetate / 6 h / 25 °C / 760 Torr
9.1: imidazole / dimethylformamide / 12 h
10.1: 2.20 g / methanol; dimethylformamide / 4 h
11.1: LiOH / tetrahydrofuran; methanol; H2O / 20 h / 25 °C
With
1H-imidazole; quinoline; lithium hydroxide; n-butyllithium; hydrogen; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trimethyl orthoformate;
Lindlar's catalyst; salcomine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol052948+
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 3.73 g / K2CO3 / methanol / 12 h / 25 °C
2.1: 99 percent / mCPBA / CH2Cl2 / 12 h / 0 °C
3.1: AcOH / monomeric (salen)Co(II)
3.2: NaBH4 / ethanol / 4 h / 50 °C
4.1: 92 percent / imidazole / dimethylformamide / 12 h / 25 °C
5.1: n-BuLi / hexane; tetrahydrofuran / 12 h / -40 °C
5.2: 74 percent / tetrahydrofuran; hexane / 0.5 h / -40 °C
6.1: 91 percent / H2; quinoline / Pd/CaCO3 (Pb poisoned) / ethyl acetate / 6 h / 25 °C / 760 Torr
7.1: imidazole / dimethylformamide / 12 h
8.1: 2.20 g / methanol; dimethylformamide / 4 h
9.1: LiOH / tetrahydrofuran; methanol; H2O / 20 h / 25 °C
With
1H-imidazole; quinoline; lithium hydroxide; n-butyllithium; hydrogen; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid;
Lindlar's catalyst; salcomine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol052948+
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: HC(OMe)3; TsOH*H2O / benzene / 8 h / Heating
2.1: 3.73 g / K2CO3 / methanol / 12 h / 25 °C
3.1: 99 percent / mCPBA / CH2Cl2 / 12 h / 0 °C
4.1: AcOH / monomeric (salen)Co(II)
4.2: NaBH4 / ethanol / 4 h / 50 °C
5.1: 92 percent / imidazole / dimethylformamide / 12 h / 25 °C
6.1: n-BuLi / hexane; tetrahydrofuran / 12 h / -40 °C
6.2: 74 percent / tetrahydrofuran; hexane / 0.5 h / -40 °C
7.1: 91 percent / H2; quinoline / Pd/CaCO3 (Pb poisoned) / ethyl acetate / 6 h / 25 °C / 760 Torr
8.1: imidazole / dimethylformamide / 12 h
9.1: 2.20 g / methanol; dimethylformamide / 4 h
10.1: LiOH / tetrahydrofuran; methanol; H2O / 20 h / 25 °C
With
1H-imidazole; quinoline; lithium hydroxide; n-butyllithium; hydrogen; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate;
Lindlar's catalyst; salcomine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol052948+
