| Abstract: | Methyl 5-amino-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside (III) has been synthesized and used as an intermediate in the preparation of the kinetin analog, methyl 5-deoxy-5-(purin-6-yl)amino-β-D-ribofuranoside (X). The related 1-substituted adenine, methyl 5- (6-aminopurin-1-yl)-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside (XIII), was prepared by cyclization of 1-benzyl-5-cyano-4-ethoxymethyleneaminoimidazole (XI) with III and subsequent debenzylation with sodium in liquid ammonia. The structures and stereochemistry of these compounds were established by a combination of ultraviolet and nuclear magnetic resonance spectroscopy. |
