
%0 Journal Article
%A Eade, RA 
%A Mcdonald, FJ 
%A Simes, JJH 
%T Extractives of Australian timbers. XV. The synthesis of 7,4'-Di-O-methylbayin
%J Australian Journal of Chemistry
%D 1975/09/01
%V 28
%N 9
%P 2011-2018
%K 
%R https://doi.org/10.1071/CH9752011
%U https://www.publish.csiro.au/paper/CH9752011 
%X The reaction between 2,6-dimethoxyphenylmagnesium bromide and tetraacetyl-&#945;-D- glucosyl chloride gave mainly &#945;-D-glucopyranosyl-2,6-dimethoxybenzene (8) and the &#946;-isomer (9). The a-isomer (8) was readily converted by acids into the /?-isomer (9), whose structure was confirmed by comparison with authentic material prepared by the degradation of 7,4?-di-O-methylbayin. The reaction of the tetraacetate of (9) with acetyl chloride in the presence of anhydrous aluminium chloride gave 3-&#946;-D-glucopyranosyl-2-hydroxy-4-methoxyacetophenone (11). Condensation of (11) with p-methoxybenzaldehyde gave the chalcone (15) which, on reaction with selenium dioxide, formed 7,4?-di-O-methylbayin (8-C-&#946;-D- glucopyranosyl-7,4?-dimethoxyflavone) (5). 
