Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

Base Information

• Chemical Name: Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester
• CAS No.: 184873-71-0
• Molecular Formula: C₂₇H₄₂O₅
• Molecular Weight: 446.627
• Mol file: 184873-71-0.mol

Synonyms:Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

Chemical Property of Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester

There total 6 articles about Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester 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: 97.0%

tetradecanoyl chloride (112-64-1) + (5S)-5-[(1S)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one (184873-70-9) → Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester (184873-71-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jm960525v

Reference yield:

O2,O3,O5,O6-tetraacetyl-L-galactonic acid-lactone (210100-08-6) → Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester (184873-71-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / H₂, Et₃N / Pd/C / ethyl acetate

2: 62 percent / SmI₂, hexamethylphosphoramide / tetrahydrofuran; ethane-1,2-diol / 1 h / Ambient temperature

3: 90 percent / 1 N HCl / tetrahydrofuran / 4 h / Heating

4: 1.) dibutyltin oxide, 2.) CsF / 1.) CHCl₃, MeOH, reflux, 3 h, 2.) a) CHCl₃, MeOH, overnight, b) DMF, RT, 48 h

5: 97 percent / pyridine, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; samarium diiodide; hydrogen; di(n-butyl)tin oxide; triethylamine; cesium fluoride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethylene glycol; ethyl acetate;

DOI:10.1021/jm960525v

Reference yield:

benzyl bromide (100-39-0) → Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester (184873-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) dibutyltin oxide, 2.) CsF / 1.) CHCl₃, MeOH, reflux, 3 h, 2.) a) CHCl₃, MeOH, overnight, b) DMF, RT, 48 h

2: 97 percent / pyridine, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; dmap; di(n-butyl)tin oxide; cesium fluoride; In dichloromethane;

DOI:10.1021/jm960525v

upstream raw materials:

tetradecanoyl chloride

(5S)-5-[(1S)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one

benzyl bromide

(S)-5-((S)-1,2-dihydroxyethyl)dihydrofuran-2(3H)-one