trans Resveratrol Penta-O-acetyl-3-β-D-glucuronide Methyl Ester

Base Information

• Chemical Name: trans Resveratrol Penta-O-acetyl-3-β-D-glucuronide Methyl Ester
• CAS No.: 490028-22-3
• Molecular Formula: C31H32O14
• Molecular Weight: 628.57738
• Mol file: 490028-22-3.mol

Synonyms:trans Resveratrol Penta-O-acetyl-3-β-D-glucuronide Methyl Ester;3-(acetyloxy)-5-[(1E)-2-[4-(acetyloxy)phenyl]ethenyl]phenyl

Chemical Property of trans Resveratrol Penta-O-acetyl-3-β-D-glucuronide Methyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 694.817°C at 760 mmHg
• Flash Point: 287.788°C
• PSA: 176.26000
• Density: 1.356g/cm³
• LogP: 2.77940
• Solubility.: Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

transResveratrolPenta-O-acetyl-3-β-D-glucuronideMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of trans Resveratrol Penta-O-acetyl-3-β-D-glucuronide Methyl Ester

There total 7 articles about trans Resveratrol Penta-O-acetyl-3-β-D-glucuronide Methyl 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: 71.0%

(E)-4-(3-acetoxy-5-hydroxystyryl)phenyl acetate (861446-14-2) + methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate (197895-54-8) → (E)-1-(3-acetoxy-5-(2,3,4-triacetyl-β-D-glucuronopyranosido)phenyl)-2-(4'-acetoxyphenyl)ethene methyl ester (490028-22-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 1.58333h; Inert atmosphere;

DOI:10.1080/00397911.2011.585733

Reference yield:

3,5-dimethoxybenzylchloride (6652-32-0) → (E)-1-(3-acetoxy-5-(2,3,4-triacetyl-β-D-glucuronopyranosido)phenyl)-2-(4'-acetoxyphenyl)ethene methyl ester (490028-22-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 10 h / 140 °C / Inert atmosphere

2: potassium hydroxide / tetrahydrofuran / 24 h / Inert atmosphere

3: magnesium; methyl iodide / diethyl ether / 45 - 190 °C / Inert atmosphere

4: triethylamine / dichloromethane / 4 h / Inert atmosphere

5: ammonium acetate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

6: boron trifluoride diethyl etherate / dichloromethane / 1.58 h / -10 °C / Inert atmosphere

With boron trifluoride diethyl etherate; ammonium acetate; magnesium; triethylamine; potassium hydroxide; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: |Arbuzov Reaction;

DOI:10.1080/00397911.2011.585733

Reference yield:

3,5-dimethoxybenzyl alcohol (705-76-0) → (E)-1-(3-acetoxy-5-(2,3,4-triacetyl-β-D-glucuronopyranosido)phenyl)-2-(4'-acetoxyphenyl)ethene methyl ester (490028-22-3)

Guidance literature:

Multi-step reaction with 7 steps

1: hydrogenchloride / water / Inert atmosphere

2: 10 h / 140 °C / Inert atmosphere

3: potassium hydroxide / tetrahydrofuran / 24 h / Inert atmosphere

4: magnesium; methyl iodide / diethyl ether / 45 - 190 °C / Inert atmosphere

5: triethylamine / dichloromethane / 4 h / Inert atmosphere

6: ammonium acetate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere

7: boron trifluoride diethyl etherate / dichloromethane / 1.58 h / -10 °C / Inert atmosphere

With hydrogenchloride; boron trifluoride diethyl etherate; ammonium acetate; magnesium; triethylamine; potassium hydroxide; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 2: |Arbuzov Reaction;

DOI:10.1080/00397911.2011.585733

upstream raw materials:

ethyl 3,5-dimethoxybenzoate

3,5-dimethoxybenzylchloride

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

methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate

Downstream raw materials:

Resveratrol-3-O-glucuronide