
%0 Journal Article
%A Eade, RA 
%A Pham, H 
%T C-Glycosylflavonoids. III. The Synthesis of 5,7,4'-Tri-O-methylvitexin (8-C-&#946;-D-Glucopyranosyl-5,7,4'-trimethoxyflavone)
%J Australian Journal of Chemistry
%D 1979/11/01
%V 32
%N 11
%P 2483-2493
%K 
%R https://doi.org/10.1071/CH9792483
%U https://www.publish.csiro.au/paper/CH9792483 
%X 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. 
