Technology Process of (6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid
There total 10 articles about (6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid 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:
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ethyl (6E,8Z,10S,11R,12E,14S,15R)-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-11-(trimethylsilyl)oxy-6,8,12-hexadecatrienoate
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1440534-65-5
(6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid
- Guidance literature:
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With
lithium hydroxide monohydrate;
In
tetrahydrofuran; water;
at 20 ℃;
for 120h;
DOI:10.1021/ol401214f
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1440534-65-5
(6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid
- Guidance literature:
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Multi-step reaction with 3 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: -78 - 20 °C
2.1: lithium chloride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) chloride / N,N-dimethyl-formamide / 20 °C
3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 120 h / 20 °C
With
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; n-butyllithium; lithium hydroxide monohydrate; diisopropylamine; copper(l) chloride; lithium chloride;
In
tetrahydrofuran; hexane; water; N,N-dimethyl-formamide;
2.1: |Stille Cross Coupling;
DOI:10.1021/ol401214f
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1440534-65-5
(6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid
- Guidance literature:
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Multi-step reaction with 5 steps
1.1: tin(II) trifluoromethanesulfonate; N-(((R)-1-methylpyrrolidin-2-yl)methyl)naphthalen-1-amine / 5 h / -78 °C
2.1: palladium 10% on activated carbon; triethylsilane / acetone / 0.67 h / 20 °C
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 20 °C
3.2: 0.5 h / -78 °C
4.1: lithium chloride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) chloride / N,N-dimethyl-formamide / 20 °C
5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 120 h / 20 °C
With
triethylsilane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tin(II) trifluoromethanesulfonate; lithium hydroxide monohydrate; N-(((R)-1-methylpyrrolidin-2-yl)methyl)naphthalen-1-amine; palladium 10% on activated carbon; sodium hexamethyldisilazane; copper(l) chloride; lithium chloride;
In
tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;
2.1: |Fukuyama Reduction / 3.2: |Wittig Olefination / 4.1: |Stille Cross Coupling;
DOI:10.1021/ol401214f
