2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid

Base Information

Chemical Name:2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid
CAS No.:1376614-73-1
Molecular Formula:C₃₀H₃₈O₅
Molecular Weight:478.629
Hs Code.:

Synonyms:2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid

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Chemical Property of 2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid

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Technology Process of 2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid

There total 23 articles about 2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic 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:

Reference yield: 82.0%

: 1375950-88-1
(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

: 1376614-73-1
2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid

Guidance literature:: (1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one; With Dess-Martin periodane; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

With sodium chlorite; sodium dihydrogen phosphate monohydrate; In water; tert-butyl alcohol; at 0 - 20 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1002/chem.201403176

Reference yield:

: C₃₀H₃₈O₄

: 1376614-73-1
2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 0 ℃; for 0.333333h;
DOI:10.1002/anie.201108749

Reference yield:

: 1375950-84-7
(3-((2R,4R,6S)-6-(but-3-ynyl)-4-(tert-butyldimethylsilyloxy)tetrahydro-2H-pyran-2-yl)prop-1-ynyl)trimethylsilane

: 1376614-73-1
2-((1S,4E,7E,10E,13R,15S)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-5-yl)acetic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 24 h / 0 - 20 °C / Inert atmosphere

1.2: 5 h / 0 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 60 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

4.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 0 - 20 °C / Inert atmosphere

4.2: -20 - 20 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / tetrahydrofuran; methanol / 2 h / 20 °C

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 1.5 h / 20 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; benzene / 1.5 h / 60 °C

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 20 °C

9.1: pyridinium p-toluenesulfonate / methanol / 20 °C

10.1: Dess-Martin periodane / dichloromethane / 0 °C

11.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 0.33 h / 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium chlorite; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; triphenylphosphine; tert-butyl alcohol; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 2.1: Negishi coupling reaction / 6.1: Mitsunobu reaction / 7.1: Stille cross-coupling / 11.1: Pinnick oxidation;
DOI:10.1002/anie.201108749