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Both enantiomers [(1'R)-6 and (1'S)-6] of N6-(1,3-dimethyl-2-butenyl)adenine and their 9-beta-D-ribofuranosides [(1"R)-16 and (1"S)-16] have been synthesized for the first time from both enantiomers of alanine (15) in nine steps. These aglycones and nucleosides, together with N6-(3-methyl-2-butenyl)adenine (5) and its 9-beta-D-ribofuranoside (18) as well as 9-beta-D-ribofuranosyl-cis-zeatin (20) and 9-(2-deoxy-beta-D-ribofuranosyl)-cis-zeatin (19), were tested for cytokinin activity in the tobacco callus bioassay. The order of their activity was 5 &gt; (1'R)-6 &gt; (1"R)-16 approximately 18 &gt; (1'S)-6 &gt; (1"S)-16 &gt; 20 &gt; 19. The bioassay results are compared with those obtained previously for the derivatives modified analogously in the N6-substituent in the cis- and trans-zeatin series.

Purines. LXII. Both Enantiomers of N6-(1,3-Dimethyl-2-butenyl)adenine and Their 9-.BETA.-D-Ribofuranosides: Synthesis and Cytokinin Activity.