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

Base Information

• Chemical Name: (S)-5-(hydroxymethyl)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one
• CAS No.: 742104-89-8
• Molecular Formula: C₂₄H₃₆O₄
• Molecular Weight: 388.547
• Mol file: 742104-89-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (S)-5-(hydroxymethyl)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-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: 60.0%

(R)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-5-[(triphenylmethoxy)methyl]-4,5-dihydrofuran-2-one (742104-88-7) → (S)-5-(hydroxymethyl)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one (742104-89-8)

Guidance literature:

With formic acid; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ol0492041

Reference yield:

(R)-{2-[(phenylmethoxy)methyl]oxiran-2-yl}(triphenylmethoxy)methane (742104-84-3) → (S)-5-(hydroxymethyl)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one (742104-89-8)

Guidance literature:

Multi-step reaction with 5 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

With quinoline; formic acid; dimethylsulfide borane complex; hydrogen; ethylenediamine; 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) → (S)-5-(hydroxymethyl)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one (742104-89-8)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ol0492041

upstream raw materials:

(R)-3-(Z)-[5-methyl-3-(2-methylpropyl)hexylidene]-5-[(phenylmethoxy)methyl]-5-[(triphenylmethoxy)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

(R)-2-[(phenylmethoxy)methyl]-1-(triphenylmethoxy)pent-4-en-2-ol

Downstream raw materials:

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