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

Base Information

• Chemical Name: (4R,5R)-4-acetyl-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one
• CAS No.: 1449307-30-5
• Molecular Formula: C₂₇H₃₂O₅
• Molecular Weight: 436.548
• Mol file: 1449307-30-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 32 articles about (4R,5R)-4-acetyl-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-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: 90.0%

(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(S)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one (1449307-29-2) → (4R,5R)-4-acetyl-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one (1449307-30-5)

Guidance literature:

With tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2013.05.091

Reference yield: 80.0%

(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 (1449307-28-1) → (4R,5R)-4-acetyl-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one (1449307-30-5)

Guidance literature:

With tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2013.05.091

Reference yield:

dimethyl 3-oxo-5-(trimethylsilyl)pent-4-ynyl phosphonate (1449307-15-6) → (4R,5R)-4-acetyl-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one (1449307-30-5)

Guidance literature:

Multi-step reaction with 10 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: tetrafluoroboric acid / water; dichloromethane / 1.67 h / 40 °C / Inert atmosphere

10.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

With bis-triphenylphosphine-palladium(II) chloride; tetrafluoroboric acid; 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; tetrapropylammonium perruthenate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; formic acid; hexane; dichloromethane; water; toluene; acetonitrile; benzene;

DOI:10.1016/j.tet.2013.05.091

upstream raw materials:

dimethyl 3-oxo-5-(trimethylsilyl)pent-4-ynyl phosphonate

(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

(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

(2S)-2-methyl-1-butanol

Downstream raw materials:

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