664351-39-7

Basic information

• Product Name: (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol
• Synonyms: (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol
• CAS NO: 664351-39-7
• Molecular Weight: 738.877
• Mol File: 664351-39-7.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol(664351-39-7)
• EPA Substance Registry System: (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol(664351-39-7)

Safety Data

• Hazardous Substances Data: 664351-39-7(Hazardous Substances Data)

Upstream product

• 918158-03-9 (1S,2S)-3-[2,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(3,4-bis-benzyloxy-phenyl)-propane-1,2-diol 
• 918157-97-8 (E)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 732298-11-2 (+)-(1S,2S)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propane-1,2-diol 
• 732298-08-7 (E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 362632-29-9 (E)-3-(3,4-bis(benzyloxy)phenyl)prop-2-en-1-ol 
• 87292-54-4 (+)-(2R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-one 
• 253336-68-4 3,4-bis(phenylmethoxy)-benzonitrile 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 100-39-0 benzyl bromide 
• 154-23-4 catechin 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 110-80-5 2-ethoxy-ethanol 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 

Downstream Products

• 223387-30-2 [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin 
• 223387-28-8 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] 
• 851775-46-7 (2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3''',4''',5'''-tri-O-benzyl)gallate 

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.

Total synthesis of 14C-labeled procyanidin B2

During the last decades, many in vitro and in vivo studies have shown the beneficial effects on health of procyanidins. However, their absorption and metabolism is still not fully understood and some aspects are still controversial. In order to have a clearer picture of the metabolism of procyanidins, the use of labelled compounds is essential. In this context, the enantioselective synthesis of 14C-radiolabelled procyanidin B2 was developed in our laboratories. It was achieved in fourteen 'hot' steps, involving as key steps the Sharpless dihydroxylation of an elaborated alkene, a stereoselective intramolecular cyclization to benzylated (+)-catechin and the condensation of two (-)-epicatechin units. 11 mCi of protected procyanidin B2 were obtained from 524 mCi of potassium [14C]cyanide. Copyright

First total synthesis of14C-labeled procyanidin B2 - A milestone toward understanding cocoa polyphenol metabolism

The idea that foods consumed for pure pleasure could provide health benefits received much recognition in the recent years. Among these foods, cocoa and dark chocolate are particularly rich in procyanidins, one of the major dietary families of polyphenols. We developed the first asymmetric total synthesis of procyanidin B2 and applied it to the preparation of a regioselectively radiolabeled 14C-analogue, which will be used to strengthen our knowledge on the metabolism of procyanidins. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthetic studies of proanthocyanidins. Part 4. The synthesis of procyanidin B1 and B4: TMSOTf-catalyzed cyclization of catechin and epicatechin condensation

Highly stereoselective synthesis of 3,4-trans series of (+)-catechin and (-)-epicatechin dimers under intramolecular condensation is described. Intramolecular condensation achieved an equimolar amount of coupling with 3,4-trans stereoselectivity and we succeeded in the synthesis of two 3,4-trans natural procyanidins, procyanidin-B1 and B4.