18469-71-1

Basic information

• Product Name: 8-β-D-Glucopyranosyl-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• Synonyms: 8-β-D-Glucopyranosyl-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• CAS NO: 18469-71-1
• Molecular Formula: C₂₄H₂₆O₁₀
• Molecular Weight: 474.45724
• Mol File: 18469-71-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8-β-D-Glucopyranosyl-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-β-D-Glucopyranosyl-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one(18469-71-1)
• EPA Substance Registry System: 8-β-D-Glucopyranosyl-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one(18469-71-1)

Safety Data

• Hazardous Substances Data: 18469-71-1(Hazardous Substances Data)

Upstream product

• 2903-76-6 5,7-dihydroxy-2-(4-hydroxy-phenyl)-8-(tetra-O-acetyl-β-D-glucopyranosyl)-chromen-4-one 
• 3681-93-4 vitexin 
• 163395-88-8 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 

Downstream Products

• 5559-28-4 5,7-dimethoxy-2-(4-methoxy-phenyl)-8-methyl-chromen-4-one 
• 102174-83-4 4-hydroxyimino-5,7-dimethoxy-2-(4-methoxy-phenyl)-4H-chromene-8-carbaldehyde-oxime 
• 20197-48-2 5,7-dimethoxy-2-(4-methoxyphenyl)-8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 94306-05-5 5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromene-8-carbaldehyde 
• 120968-77-6 5,7-dimethoxy-2-(4-methoxy-phenyl)-8-[tetrakis-O-(4-nitro-benzoyl)-β-D-glucopyranosyl]-chromen-4-one 

Relevant articles and documents

Glycosyl Imidates, 69. - Synthesis of Flavone C-Glycosides Vitexin, Isovitexin, and Isoembigenin

2-Hydroxy-4,6-dimethoxyacetophenone (4) was glycosylated with O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) trichloroacetimidate (5) and trimethylsilyl triflate as promoter to yield directly the C-glycoside 6.Construction of the flavone system by application of a Baker-Venkataraman-type rearrangement followed by deprotection yielded isoembigenin (2).Glycosylation of 4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone (17) with the trichloroacetimidate 5 afforded the O-glycoside intermediate 18 which was converted via Fries rearrangement into the C-glycoside 21.Applying again the Baker-Venkataraman rearrangement and cyclization gave isovitexin and vitexin derivatives 25 and 26, which were completely deprotected to yield isovitexin (1b) and vitexin (1a), respectively. - Key Words: Glycosides / Flavones / Vitexin / Isovitexin / Isoembigenin / Carbohydrates / Trichloroacetimidates / Fries rearrangement / Baker-Venkataraman rearrangement