664351-41-1

Basic information

• Product Name: (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan
• Synonyms: (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan
• CAS NO: 664351-41-1
• Molecular Weight: 780.915
• Mol File: 664351-41-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan(664351-41-1)
• EPA Substance Registry System: (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan(664351-41-1)

Safety Data

• Hazardous Substances Data: 664351-41-1(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 478796-20-2 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol 
• 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 
• 476312-06-8 [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin 
• 664351-48-8 [4,8']-2,3-trans-3,4-trans:2',3'-cis-octa-O-benzyl-3-O-acetyl-(+)-catechin-(-)-epicatechin 

Relevant articles and documents

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.