478796-20-2

Basic information

• Product Name: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol
• Synonyms: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol
• CAS NO: 478796-20-2
• Molecular Weight: 738.877
• Mol File: 478796-20-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol(478796-20-2)
• EPA Substance Registry System: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol(478796-20-2)

Safety Data

• Hazardous Substances Data: 478796-20-2(Hazardous Substances Data)

Upstream product

• 110-80-5 2-ethoxy-ethanol 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 100-44-7 benzyl chloride 

Downstream Products

• 1352123-17-1 (2R,3S,4S)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2''-ethoxy-ethoxy)-flavan 
• 1352123-21-7 C₅₄H₅₃BO₁₀ 
• 1352123-18-2 (2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan 
• 29106-49-8 procyanidin B₂ 
• 828249-32-7 (2R,3S,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate 
• 223387-28-8 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] 
• 664351-43-3 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8β)-[5,7,3',4'-tetra-O-benzyl-(+)-catechin] 
• 596829-26-4 Pentanedioic acid (2R,3S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-yl ester (2R,3S,4S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-yl ester 
• 664351-41-1 (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan 

Relevant articles and documents

Procyanidin oligomers. A new method for 4→8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy

Interest in the synthesis of procyanidin (catechin or epicatechin) oligomers that contain the 4→8 interflavan linkage remains high, principally due to research into their health effects. A novel coupling utilising a C8-boronic acid as a directing group was developed in the synthesis of natural procyanidin B3 (i.e., 3,4-trans-(+)-catechin-4α→8-(+)- catechin dimer). The key interflavan bond was forged using a novel Lewis acid-promoted coupling of C4-ether 6 with C8-boronic acid 16 to provide the α-linked dimer with high diastereoselectivity. Through the use of a boron protecting group, the new coupling procedure was extended to the synthesis of a protected procyanidin trimer analogous to natural procyanidin C2.

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. 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.

Synthetic studies of proanthocyanidins. Part 2: Stereoselective gram-scale synthesis of procyanidin-B3

A stereoselective synthesis of procyanidin-B3, a condensed catechin dimer, is described. Condensation of benzylated catechin with various 4-O-alkylated flavan-3,4-diol derivatives as an electrophile in the presence of a Lewis acid led to protected procyanidin-B3 and its diastereomer. In particular, the reaction using (2R,3S,4S)-3-acetoxy-5,7,3′,4′-tetrabenzyloxy-4-(2″- ethoxyethoxy)flavan as an electrophile in the presence of TMSOTf at -78°C afforded octa-O-benzylated procyanidin-B3 with high levels of stereoselectivity and in excellent isolation yields. Furthermore, we succeeded in a stereoselective gram-scale synthesis of protected procyanidin-B3.