1-O-Levulinoyl Resveratrol Diacetate

Base Information

• Chemical Name: 1-O-Levulinoyl Resveratrol Diacetate
• CAS No.: 861446-23-3
• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.423
• Mol file: 861446-23-3.mol

Synonyms:3,4'-diacetoxy-5-levulinoxystilbene

Chemical Property of 1-O-Levulinoyl Resveratrol Diacetate

Chemical Property:

• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

99% ^*data from raw suppliers

1-O-Levulinoyl Resveratrol Diacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-O-Levulinoyl Resveratrol Diacetate is a Levulinate protected derivative of Resveratrol (R150000), used in the preparation of hydroxylated stilbenes, important antioxidant disease preventative agents isolated from grape skins and other dietary sources.

Technology Process of 1-O-Levulinoyl Resveratrol Diacetate

There total 4 articles about 1-O-Levulinoyl Resveratrol Diacetate 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: 70.0%

3-acetoxy-5-levulinoxybenzoic chloride (861446-22-2) + p-acetoxystyrene (2628-16-2) → 3,4'-diacetoxy-5-levulinoxystilbene (861446-23-3)

Guidance literature:

With 4-methyl-morpholine; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; palladium diacetate; In xylene; at 120 ℃; for 3.5h;

DOI:10.1016/j.tetlet.2006.05.065

Reference yield:

3-acetoxy-5-levulinoxybenzoic acid (861446-21-1) → 3,4'-diacetoxy-5-levulinoxystilbene (861446-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / benzotriazole; thionyl chloride / CH₂Cl₂ / 0.17 h

2: 70 percent / 1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride; N-methylmorpholine / Pd(OAc)2 / xylene / 3.5 h / 120 °C

With 4-methyl-morpholine; 1,2,3-Benzotriazole; thionyl chloride; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; palladium diacetate; In dichloromethane; xylene; 2: decarbonylative Heck coupling;

DOI:10.1016/j.tetlet.2006.05.065

Reference yield:

3,5-Dihydroxybenzoic acid (99-10-5) → 3,4'-diacetoxy-5-levulinoxystilbene (861446-23-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / NaOH / H₂O / 0.67 h

2: 96 percent / pyridine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

3: 45 percent / benzotriazole; thionyl chloride / CH₂Cl₂ / 0.17 h

4: 70 percent / 1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride; N-methylmorpholine / Pd(OAc)2 / xylene / 3.5 h / 120 °C

With 4-methyl-morpholine; pyridine; 1,2,3-Benzotriazole; sodium hydroxide; thionyl chloride; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; palladium diacetate; In dichloromethane; water; xylene; 4: decarbonylative Heck coupling;

DOI:10.1016/j.tetlet.2006.05.065

upstream raw materials:

3-acetoxy-5-levulinoxybenzoic chloride

p-acetoxystyrene

3-acetoxy-5-levulinoxybenzoic acid

3,5-Dihydroxybenzoic acid

Downstream raw materials:

(E)-4-(3-acetoxy-5-hydroxystyryl)phenyl acetate

Refernces

• 1、 Andrus, Merritt B.,Liu, Jing. "Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings". . p. 5811 - 5814. Retrieved 2007/10/03.