(+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Base Information

• Chemical Name: (+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate
• CAS No.: 1392130-58-3
• Molecular Formula: C₁₄H₁₆O₆
• Molecular Weight: 280.277
• Mol file: 1392130-58-3.mol

Synonyms:(+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Chemical Property of (+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate

There total 10 articles about (+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate 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: 67.0%

(+)-(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl (E)-3-[3,4-bis(methoxymethoxy)phenyl]acrylate → (+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate (1392130-58-3)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1055/s-0035-1561588

Reference yield: 5.0%

(+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate → (+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate (1392130-58-3)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 25 ℃; for 2.5h; Inert atmosphere;

DOI:10.1055/s-0035-1561588

Reference yield:

(+/-)-2-hydroxy-3-methylenesuccinic acid dimethyl ester (50592-73-9) → (+)-(S)-3,4-dihydroxy-2-methylenebutyl (E)-3-(3,4-dihydroxyphenyl)acrylate (1392130-58-3)

Guidance literature:

Multi-step reaction with 7 steps

1: Amano PS / benzene / 48 h / 25 °C / Resolution of racemate

2: 1H-imidazole / dichloromethane / 6 h / 0 - 25 °C / Inert atmosphere

3: diisobutylaluminium hydride / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 0 - 25 °C

5: tetrahydrofuran / 4 h / 0 - 25 °C

6: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dmap / dichloromethane / 6 h / 0 - 25 °C / Inert atmosphere

7: toluene-4-sulfonic acid / methanol / 3 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; Amano PS; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;

DOI:10.1055/s-0035-1561588

upstream raw materials:

(+)-(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

(+/-)-2-hydroxy-3-methylenesuccinic acid dimethyl ester

(S)-2-acetoxy-3-methylenesuccinic acid dimethyl ester

(S)-2-hydroxy-3-methylenesuccinic acid dimethyl ester