381686-11-9

Basic information

• Product Name: 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5,7-dimethoxy-4H-1-benzopyran-4-one
• Synonyms: 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5,7-dimethoxy-4H-1-benzopyran-4-one
• CAS NO: 381686-11-9
• Molecular Weight: 1017.18
• Mol File: 381686-11-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5,7-dimethoxy-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5,7-dimethoxy-4H-1-benzopyran-4-one(381686-11-9)
• EPA Substance Registry System: 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5,7-dimethoxy-4H-1-benzopyran-4-one(381686-11-9)

Safety Data

• Hazardous Substances Data: 381686-11-9(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 381686-10-8 2-(3,4-bis-benzyloxyphenyl)-8-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one 
• 39548-86-2 1‐(2‐(benzyloxy)‐4,6‐dihydroxyphenyl)ethan‐1‐one 
• 10299-59-9 1‐(2‐(benzyloxy)‐6‐hydroxy‐4‐methoxyphenyl)ethan‐1‐one 
• 381686-09-5 3,4,6'-tris-benzyloxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2'-hydroxy-4'-methoxychalcone 
• 169566-44-3 6-benzyloxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxy-4-methoxyacetophenone 

Relevant articles and documents

Synthesis of 8-C-glucosylflavones

The syntheses of orientin, parkinsonin A, isoswertiajaponin, and parkinsonin B, which are 8-C-β-D-glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone, 5-methyl orientin, 7-methyl orientin, and 5,7-dimethyl orientin, respectively, are reported herein. The C-glucosyl phloroacetophenone derivatives were obtained via a regio- and stereoselective O → C glycosyl rearrangement. Aldol condensation of the C-glucosyl phloroacetophenone derivatives with 3,4-bisbenzyloxybenzaldehyde afforded the corresponding C-glucosylchalcones. Construction of the flavone system by reaction with I2-Me2SO, followed by the elimination of the 5-benzyl protecting group in the flavone structure, yielded an orientin derivative and a isoswertiajaponin derivative. Methylation of the orientin derivatives with dimethyl sulfate afforded the parkinsonin A derivative, the isoswertiajaponin derivative, and the parkinsonin B derivative. Finally, hydrogenolysis of these C-glucosylflavone derivatives led to the four 8-C-glucosylflavones. The NMR spectra of these C-glucosylflavones showed a duplication of signals corresponding to a major rotamer, along with a minor one. Based on NOESY experiments in Me2SO at ambient temperature, they adopted conformations in which the H-2″ and H-4″ protons in the glucose moiety were oriented toward the B-ring in the flavone structure.