294203-79-5

Basic information

• Product Name: (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one
• Synonyms: (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one
• CAS NO: 294203-79-5
• Molecular Weight: 1081.27
• Mol File: 294203-79-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one(294203-79-5)
• EPA Substance Registry System: (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one(294203-79-5)

Safety Data

• Hazardous Substances Data: 294203-79-5(Hazardous Substances Data)

Upstream product

• 294203-76-2 (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman 
• 104495-20-7 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride 
• 80152-99-4 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose 
• 294203-78-4 (2R,3S,4S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-ol 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 

Downstream Products

• 29838-67-3 astilbin 

Relevant articles and documents

Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: Glycoside-flavonoid analogy

Cationic metallocene species, generated from Cp2MCl2 and AgClO4 (M=Zr, Hf), were used for the glycosylation of catechin derivative 2, enabling a concise synthesis of a glycosyl flavonoid, astilbin (1). Further study revealed the efficiency of this Lewis acidic species for SN1-type activation of the C(4) position of catechin derivative 11, enabling selective substitution with various nucleophiles.

First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2-AgClO4, and subsequent oxidation of the C(4)position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd.