294203-72-8

Basic information

• Product Name: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol
• Synonyms: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol
• CAS NO: 294203-72-8
• Molecular Weight: 680.797
• Mol File: 294203-72-8.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol(294203-72-8)
• EPA Substance Registry System: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol(294203-72-8)

Safety Data

• Hazardous Substances Data: 294203-72-8(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 

Downstream Products

• 137624-12-5 5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin 
• 137550-06-2 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin 
• 23567-23-9 procyanidin B₃ 
• 476312-04-6 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan 

Relevant articles and documents

Synthesis of procyanidin B1, B2, and B4 and their anti-inflammatory activity: The effect of 4-alkoxy group of catechin and/or epicatechin electrophiles for condensation

Abstract: Procyanidin B1, B2, and B3 were synthesized based on a Yb(OTf)3 catalyzed equimolar condensation using methoxy and/or 4-(2-ethoxyethoxy) drivatives as electrophiles. The anti-inflammatory effect of synthetic procyanidin B1, B2, and B4 on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. Procyanidin B1, B2, B 4 suppressed TPA-induced inflammation of mouse ears by 48%, 34%, and 29%, respectively, at a dose of 200 μg. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used antiinflammatory agent.

Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: Glycoside-flavonoid analogy

Cationic metallocene species, generated from Cp2MCl2 and AgClO4 (M=Zr, Hf), were used for the glycosylation of catechin derivative 2, enabling a concise synthesis of a glycosyl flavonoid, astilbin (1). Further study revealed the efficiency of this Lewis acidic species for SN1-type activation of the C(4) position of catechin derivative 11, enabling selective substitution with various nucleophiles.

Synthetic studies of proanthocyanidins. Highly stereoselective synthesis of the catechin dimer, procyanidin-B3.

A stereoselective synthesis of benzylated procyanidin-B3, a condensed catechin dimer, is described. Condensation of 5,7,3',4'-tetrabenzylcatechin with (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan as an electrophile in the presence of TiCl4 led to octabenzylated procyanidin-B3 stereoselectively.

First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2-AgClO4, and subsequent oxidation of the C(4)position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd.