(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

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Chemical Name:(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one
CAS No.:1449307-28-1
Molecular Formula:C₂₇H₃₄O₅
Molecular Weight:438.564
Hs Code.:

Synonyms:(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

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Chemical Property of (4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

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Technology Process of (4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

There total 27 articles about (4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one 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: 64.0%

: 1449307-24-7
(4R,5R)-4-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

: 1449307-28-1
(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

Guidance literature:: With ammonium fluoride; In 1,4-dioxane; water; at 0 ℃; for 1.5h; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.091

Reference yield: 45.0%

: (4R,5R)-4-[(1R)-1-(tert-butyldimethylsiloxy)ethyl]-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-3-hydroxy-4,5-(isopropylidenedioxy)-3-phenylcyclopent-1-enyl dimethyl phosphate

: 1449307-28-1
(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

Guidance literature:: With tetrafluoroboric acid; In dichloromethane; water; at 40 ℃; for 1.66667h; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.091

Reference yield:

: 1449307-15-6
dimethyl 3-oxo-5-(trimethylsilyl)pent-4-ynyl phosphonate

: 1449307-28-1
(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: toluene-4-sulfonic acid / methanol / 6 h / Reflux; Inert atmosphere

2.1: sodium tetraborate decahydrate / water; formic acid / 3 h / 40 °C / Inert atmosphere

3.1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere

4.1: trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; 2,6-di-tert-butyl-4-methyl-phenol / toluene / 44 h / 50 °C / Inert atmosphere; Darkness

5.1: bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri-tert-butyl phosphine / tetrahydrofuran; toluene / 22 h / 0 - 55 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

6.2: -78 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / acetonitrile; water / 16 h / 20 °C / Inert atmosphere

8.1: 18-crown-6 ether; potassium carbonate / benzene / 3.5 h / 60 °C / Inert atmosphere

9.1: ammonium fluoride / water; 1,4-dioxane / 1.5 h / 0 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; ammonium fluoride; n-butyllithium; sodium tetraborate decahydrate; trifuran-2-yl-phosphane; 18-crown-6 ether; tri-tert-butyl phosphine; 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; toluene-4-sulfonic acid; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; formic acid; hexane; water; toluene; acetonitrile; benzene;
DOI:10.1016/j.tet.2013.05.091