(E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone

Base Information

• Chemical Name: (E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone
• CAS No.: 172843-43-5
• Molecular Formula: C₂₉H₄₄O₅
• Molecular Weight: 472.665
• Mol file: 172843-43-5.mol

Synonyms:(E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone

Chemical Property of (E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone

There total 11 articles about (E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone 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: 99.0%

acetic anhydride (108-24-7) + 4-Benzyloxymethyl-4-hydroxymethyl-3-tetradec-(E)-ylidene-dihydro-furan-2-one (220492-74-0) → (E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone (172843-43-5)

Guidance literature:

With pyridine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm950276v

Reference yield:

myristylaldehyde (124-25-4,511542-15-7) → (E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone (172843-43-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sodium bis(trimethylsilyl)amide, 2.) hexamethylphosphoramide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) -48 deg C, 1 h

2: 1.) methanesulfonyl chloride, triethylamine, 2.) triethylamine / 1.) CH₂Cl₂, a) 0 deg C, 30 min, b) RT, 30 min, 2.) CH₂Cl₂, RT, 24 h

3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

4: 99 percent / pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm950276v

Reference yield:

benzyl bromide (100-39-0) → (E)-4-(acetyloxymethyl)-4-<(benzyloxy)methyl>-3-tetradecanylidenetetrahydro-2-furanone (172843-43-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 8 h

2: 94 percent / water, N-methylmorpholine N-oxide, osmium tetraoxide, sodium metaperiodate / acetone; 2-methyl-propan-2-ol / 20 h / Ambient temperature

3: 98 percent / sodium borohydride / tetrahydrofuran; H₂O / 0.5 h

4: 96 percent / imidazole / dimethylformamide / 14 h

5: 1.) sodium bis(trimethylsilyl)amide, 2.) hexamethylphosphoramide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) -48 deg C, 1 h

6: 1.) methanesulfonyl chloride, triethylamine, 2.) triethylamine / 1.) CH₂Cl₂, a) 0 deg C, 30 min, b) RT, 30 min, 2.) CH₂Cl₂, RT, 24 h

7: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

8: 99 percent / pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/jm950276v

upstream raw materials:

acetic anhydride

4-Benzyloxymethyl-4-hydroxymethyl-3-tetradec-(E)-ylidene-dihydro-furan-2-one

myristylaldehyde

benzyl bromide

Refernces