
TY  - JOUR
A1  - Eade, RA 
A1  - Pham, H 
T1  - C-Glycosylflavonoids. III. The Synthesis of 5,7,4'-Tri-O-methylvitexin (8-C-&#946;-D-Glucopyranosyl-5,7,4'-trimethoxyflavone)
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1979
VL  - 32
IS  - 11
SP  - 2483
EP  - 2493
KW  - 
UR  - https://doi.org/10.1071/CH9792483 
N2  - The reaction between 1,3,5-trimethoxybenzene and tetraacetyl-&#945;-D-glucosyl bromide in the presence of zinc oxide gave &#946;-D-glucopyranosyl-2,4,6-trimethoxybenzene tetraacetate (12). The tetraacetate (12) was converted by acetic anhydride and anhydrous aluminium chloride into 3-&#946;-D- glucopyranosyl-2-hydroxy-4,6-dimethoxyacetophenone tetraacetate (15). Condensation of the acetophenone tetraacetate (15) with 4-methoxybenzaldehyde in the presence of sodium hydroxide gave 3'-&#946;-D-glucopyranosyl-2'-hydroxy-4,4',6'-trimethoxychacone (6). Reaction of the chalcone (6) with selenium dioxide gave 8-C-&#946;-D-glucopyranosyl-5,7,4'-trimethoxyflavone (5,7,4'-tri-O- methylvitexin)(10). The chemical shifts of the olefinic protons of chalcones are discussed. 
ER  -

