(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone

Base Information

Chemical Name:(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone
CAS No.:1440534-69-9
Molecular Formula:C₁₈H₂₃NO₄
Molecular Weight:317.385
Hs Code.:

Synonyms:(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone

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Chemical Property of (S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone

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Technology Process of (S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone

There total 1 articles about (S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone 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: 92.0%

: (S)-4-benzyl-3-{(1E,3E)-1[(tert-butyldimethylsilyl)oxy]-2-methylpenta-1,3-diene-1-yl}oxazolidin-2-one

: 75-07-0,9002-91-9
acetaldehyde

: 1440534-69-9
(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone

Guidance literature:: acetaldehyde; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h;

(S)-4-benzyl-3-{(1E,3E)-1[(tert-butyldimethylsilyl)oxy]-2-methylpenta-1,3-diene-1-yl}oxazolidin-2-one; In dichloromethane; at -78 - -50 ℃; diastereoselective reaction;
DOI:10.1021/ol401214f

Reference yield: 97.0%

: 994-30-9
triethylsilyl chloride

: 1440534-69-9
(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone

: 1440534-70-2
(S)-4-benzyl-3-((2E,4S,5R)-2,4-dimethyl-5-(triethylsilyl)oxy-2-hexenoyl)-2-oxazolidinone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/ol401214f

Reference yield:

: 1440534-69-9
(S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone

: 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:: Multi-step reaction with 7 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C

3.1: tin(II) trifluoromethanesulfonate; N-(((R)-1-methylpyrrolidin-2-yl)methyl)naphthalen-1-amine / 5 h / -78 °C

4.1: palladium 10% on activated carbon; triethylsilane / acetone / 0.67 h / 20 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 20 °C

5.2: 0.5 h / -78 °C

6.1: lithium chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) chloride / N,N-dimethyl-formamide / 20 °C

7.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 120 h / 20 °C

With 1H-imidazole; 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; diisobutylaluminium hydride; copper(l) chloride; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 4.1: |Fukuyama Reduction / 5.2: |Wittig Olefination / 6.1: |Stille Cross Coupling;
DOI:10.1021/ol401214f