
TY  - JOUR
A1  - Cowley, DE 
A1  - Duke, CC 
A1  - Liepa, AJ 
A1  - Macleod, JK 
A1  - Letham, DS 
T1  - The Structure and Synthesis of Cytokinin Metabolites. 1. The 7- and 9-&#946;-D-Glucofuranosides and Pyranosides of Zeatin and 6-Benzylaminopurine
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 5
SP  - 1095
EP  - 1111
KW  - 
UR  - https://doi.org/10.1071/CH9781095 
N2  - 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. 
ER  -

