
%0 Journal Article
%A Cowley, DE 
%A Duke, CC 
%A Liepa, AJ 
%A Macleod, JK 
%A Letham, DS 
%T The Structure and Synthesis of Cytokinin Metabolites. 1. The 7- and 9-&#946;-D-Glucofuranosides and Pyranosides of Zeatin and 6-Benzylaminopurine
%J Australian Journal of Chemistry
%D 1978/05/01
%V 31
%N 5
%P 1095-1111
%K 
%R https://doi.org/10.1071/CH9781095
%U https://www.publish.csiro.au/paper/CH9781095 
%X The structures of the major stable plant metabolites of the cytokinins zeatin and 6-benzylaminopurine have been confirmed by synthesis to be 7- and 9-&#946;-D-glucopyranosides. The small quantities of metabolites initially isolated (< 100 &#956;g) precluded assignment of the glucose ring size or configuration of the anomeric linkage so that synthesis of both the furanose and pyranose forms of 7-&#946;-D- and 9-&#946;-D-glucosylzeatin and 6-benzylaminopurine was undertaken which allowed direct u.v., m.s. and t.l.c. comparison with the metabolites. Numerous synthetic routes to the unusual 7-glucosides of the two cytokinins were explored, the most successful utilizing a one-pot pyrimidine ring closure of an imidazole derivative to afford directly in high yield the required 7-glucosides of zeatin and 6-benzylaminopurine. 
