(3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

Base Information

• Chemical Name: (3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate
• CAS No.: 1373247-32-5
• Molecular Formula: C₁₉H₁₈O₅
• Molecular Weight: 326.349
• Mol file: 1373247-32-5.mol

Synonyms:(3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

Chemical Property of (3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

There total 2 articles about (3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate 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: 90.0%

benzyl chloroformate (501-53-1,94274-21-2) + (S)-4-(3-methoxyphenyl)dihydrofuran-2(3H)-one → (3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate (1373247-32-5)

Guidance literature:

(S)-4-(3-methoxyphenyl)dihydrofuran-2(3H)-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

benzyl chloroformate; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/anie.201109221

Reference yield:

2-bromo-3'-methoxyacetophenone (5000-65-7) → (3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate (1373247-32-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / tetrahydrofuran / 20 - 50 °C / Inert atmosphere

2.1: (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; copper(l) chloride; sodium t-butanolate; tert-butyl alcohol / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.17 h / -78 °C / Inert atmosphere

With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; potassium carbonate; copper(l) chloride; lithium hexamethyldisilazane; sodium t-butanolate; tert-butyl alcohol; In tetrahydrofuran;

DOI:10.1002/anie.201109221

Reference yield: 90.0%

(3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate (1373247-32-5) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate (1373247-33-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/anie.201109221

upstream raw materials:

benzyl chloroformate

2-bromo-3'-methoxyacetophenone

Downstream raw materials:

(5S,9R)-9-(3-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione

(5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione

(5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-methyl-1,7-diazaspiro[4.4]nonane-2,6,8-trione

C₁₅H₁₆Br₂N₂O₄