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
• Article Data: 4

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

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

Downstream Products

• 664351-41-1 (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan 
• 1352123-17-1 (2R,3S,4S)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2''-ethoxy-ethoxy)-flavan 
• 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 
• 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] 

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.

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.