(2R,3S)-catechin 4'-β-D-glucuronic acid

Base Information

• Chemical Name: (2R,3S)-catechin 4'-β-D-glucuronic acid
• CAS No.: 1146696-33-4
• Molecular Formula: C₂₁H₂₂O₁₂
• Molecular Weight: 466.398
• Mol file: 1146696-33-4.mol

Synonyms:(2R,3S)-catechin 4'-β-D-glucuronic acid

Chemical Property of (2R,3S)-catechin 4'-β-D-glucuronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-catechin 4'-β-D-glucuronic acid

There total 5 articles about (2R,3S)-catechin 4'-β-D-glucuronic 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: 78.0%

(2R,3S)-5,7,3'-tri-O-benzylcatechin 4'-β-D-glucuronic acid (1422182-76-0) → (2R,3S)-catechin 4'-β-D-glucuronic acid (1146696-33-4)

Guidance literature:

With Pd(OH)2/C; hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 6h; under 760.051 Torr;

Reference yield:

catechin (154-23-4) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → catechin-3'-O-β-D-glucuronide (853728-25-3) + (+)-catechin-5-O-β-glucuronide (242807-38-1) + (2R,3S)-catechin 4'-β-D-glucuronic acid (1146696-33-4) + (+)-catechin 5-O-β-glucuronide

Guidance literature:

catechin; 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester; With potassium carbonate; In acetone; at 20 ℃; for 2h;

With formic acid; In water; acetone; regioselective reaction; Further stages; Cooling;

DOI:10.1021/jf803140h

Reference yield:

(2R,3S)-5,7,3'-tri-O-benzyl-3-O-acetylcatechin (1422182-74-8) → (2R,3S)-catechin 4'-β-D-glucuronic acid (1146696-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 17 h / 0 - 20 °C

2.1: potassium hydroxide; water / tetrahydrofuran / 8 h / 20 °C

2.2: pH 6

3.1: Pd(OH)2/C; hydrogen / methanol; tetrahydrofuran / 6 h / 20 °C / 760.05 Torr

With Pd(OH)2/C; boron trifluoride diethyl etherate; water; hydrogen; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

catechin

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

(2R,3S)-5,7,3'-tri-O-benzyl-3-O-acetylcatechin

(2R,3S)-5,7,3'-tri-O-benzyl-3-acetylcatechin 4'-(2,3,4-tri-O-acetyl-β-D-methyl glucuronate)