(R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate

Base Information

• Chemical Name: (R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate
• CAS No.: 742104-90-1
• Molecular Formula: C₂₉H₄₄O₅
• Molecular Weight: 472.665
• Mol file: 742104-90-1.mol

Synonyms:(R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate

Chemical Property of (R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate

There total 6 articles about (R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate 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: 100.0%

pivaloyl chloride (3282-30-2) + (S)-5-(hydroxymethyl)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one (742104-89-8) → (R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate (742104-90-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol0492041

Reference yield:

(R)-{2-[(phenylmethoxy)methyl]oxiran-2-yl}(triphenylmethoxy)methane (742104-84-3) → (R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate (742104-90-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 79 percent / ethylene diamine / dimethylsulfoxide / 2 h / 20 °C

2.1: 97 percent / quinoline; H₂ / Lindlar catalyst / hexane / 2 h

3.1: BH₃*SMe₂ / tetrahydrofuran / 24 h / 20 °C

3.2: 48 percent / PCC / CH₂Cl₂ / 24 h

4.1: LHMDS / tetrahydrofuran / 1 h / -78 °C

4.2: Et₃N; MsCl / CH₂Cl₂ / 5 h / 20 °C

4.3: 43 percent / DBU / CH₂Cl₂ / 0.17 h

5.1: 60 percent / formic acid / CH₂Cl₂ / 24 h / 20 °C

6.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With quinoline; dmap; formic acid; dimethylsulfide borane complex; hydrogen; ethylenediamine; triethylamine; lithium hexamethyldisilazane; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ol0492041

Reference yield:

(R)-2-[(phenylmethoxy)methyl]-1-(triphenylmethoxy)pent-4-yn-2-ol (742104-85-4) → (R)-{4-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2,3-dihydrofur-2-yl}methyl 2,2-dimethylpropanoate (742104-90-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / quinoline; H₂ / Lindlar catalyst / hexane / 2 h

2.1: BH₃*SMe₂ / tetrahydrofuran / 24 h / 20 °C

2.2: 48 percent / PCC / CH₂Cl₂ / 24 h

3.1: LHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: Et₃N; MsCl / CH₂Cl₂ / 5 h / 20 °C

3.3: 43 percent / DBU / CH₂Cl₂ / 0.17 h

4.1: 60 percent / formic acid / CH₂Cl₂ / 24 h / 20 °C

5.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With quinoline; dmap; formic acid; dimethylsulfide borane complex; hydrogen; triethylamine; lithium hexamethyldisilazane; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol0492041

upstream raw materials:

pivaloyl chloride

(S)-5-(hydroxymethyl)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one

(R)-{2-[(phenylmethoxy)methyl]oxiran-2-yl}(triphenylmethoxy)methane

(R)-5-[(phenylmethoxy)methyl]-5-[(triphenylmethoxy)methyl]-4,5-dihydrofuran-2(3H)-one