(2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid

Base Information

• Chemical Name: (2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid
• CAS No.: 1400219-41-1
• Molecular Formula: C₁₈H₁₆O₅
• Molecular Weight: 312.322
• Mol file: 1400219-41-1.mol

Synonyms:

Chemical Property of (2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid

There total 4 articles about (2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid 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: 7.0%

benzaldehyde (100-52-7) + 3-(4-methoxyphenyl)dihydrofuran-2,5-dione (32856-59-0,67295-42-5) → (2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid (1400219-41-1)

Guidance literature:

With C₃₈H₃₂F₆N₄O₃; In tert-butyl methyl ether; at -15 ℃; for 93h; Inert atmosphere;

DOI:10.1039/c2cc32147e

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid (1400219-41-1)

Guidance literature:

Multi-step reaction with 5 steps

1: piperidine / toluene / 16 h / Reflux

2: ethanol; water / 16 h / Reflux

3: water; potassium hydroxide / ethanol / 16 h / Reflux

4: acetic anhydride / 16 h / 80 °C / Inert atmosphere

5: C₃₈H₃₂F₆N₄O₃ / tert-butyl methyl ether / 93 h / -15 °C / Inert atmosphere

With piperidine; C₃₈H₃₂F₆N₄O₃; water; acetic anhydride; potassium hydroxide; In ethanol; tert-butyl methyl ether; water; toluene;

DOI:10.1039/c2cc32147e

Reference yield:

2-(4-methoxyphenyl)succinic acid (13565-23-6,38971-62-9,117603-61-9,6331-59-5) → (2S,3S)-3-(4-methoxyphenyl)-5-oxo-2-phenyltetrahydrofuran-3-carboxylic acid (1400219-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic anhydride / 16 h / 80 °C / Inert atmosphere

2: C₃₈H₃₂F₆N₄O₃ / tert-butyl methyl ether / 93 h / -15 °C / Inert atmosphere

With C₃₈H₃₂F₆N₄O₃; acetic anhydride; In tert-butyl methyl ether;

DOI:10.1039/c2cc32147e

upstream raw materials:

2-(4-methoxyphenyl)succinic acid

diethyl-2-(4-methoxybenzylidene)malonate

benzaldehyde

3-(4-methoxyphenyl)dihydrofuran-2,5-dione

Refernces