137624-12-5

Basic information

• Product Name: 5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin
• Synonyms: 5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin
• CAS NO: 137624-12-5
• Molecular Weight: 1299.53
• Mol File: 137624-12-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin(137624-12-5)
• EPA Substance Registry System: 5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin(137624-12-5)

Safety Data

• Hazardous Substances Data: 137624-12-5(Hazardous Substances Data)

Upstream product

• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 137624-11-4 (2R,3S,4S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3,4-diol 
• 1217257-69-6 3’,4’,5,7-tetra-O-benzyl-4β-O-propargylcatechin 
• 596829-27-5 C₉₀H₇₆O₁₄ 
• 664351-41-1 (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan 
• 294203-72-8 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol 

Downstream Products

• 51196-37-3 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin 

Relevant articles and documents

Procyanidin B3 synthesis: a study of leaving group and Lewis acid activator effects upon interflavan bond formation

A range of electrophilic ethers were prepared via DDQ oxidation and alcoholic trapping (propanol, crotyl alcohol and propargyl alcohol) at the C4 position of (+)-catechin. The Lewis acid-mediated C4-substitution of each of these ethers was examined and it was found that the propargyl ether was the best overall electrophile. A range of Lewis acids were then examined as activators and it was found that BF3·OEt2 was the best in terms of both yield and stereochemical control at the C4 position. This newly developed set of conditions was then used to prepare the natural product nutraceutical procyanidin B3 with complete control of stereochemistry.

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.

Deuterium labeled procyanidin syntheses

Deuterium-labeled procyanidins have been prepared by hemisynthesis from taxifolin in order to investigate their metabolism in human. The structures of the desired deuterated natural compounds B3 10D (R1 = D, R2 = H) and B4 13D (R1 = D, R2 = H) were proven by spectroscopic and physical properties means, including 2H NMR spectrum. By-products with unatural absolute configuration at some centers were also formed along the process and were characterised.