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
• Article Data: 4

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.

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.