Substitution effect of purine nucleosides on diisobutylaluminum hybride reduction.
It is reported that the diisobutylaluminum hydride (DIBALH) reduction of inosine and adenosine derivatives (1a and 1d) causes cleavage of the ribose moiety to give the corresponding 9-ribitylhypoxanthine (2a) and 9-ribityladenine (2d), respectively. The substitution effect of purine nucleosides on the reduction was investigated. O6-alkylinosine derivatives (1b and 1c) were reduced in good yields like 1a. Introduction of methyl group into the N6-position of adenosine (1d), however, greatly reduced the reactivity toward DIBALH. The reduction of 7-deazainosine (3a) and 7-deazaadenosine (3b) hardly proceeded. These results suggest that oxygenophilicity of aluminum atom facilitates coordination of DIBALH to the 7-ring nitrogen atom and accelerate a cleavage of the ribose.
Hirota
K
K
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Japan.
Monguchi
Y
Y
Sako
M
M
Kitade
Y
Y
D001665:Binding Sites; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D019163:Reducing Agents / Q000737:chemistry*
D009942:Organometallic Compounds; D011684:Purine Nucleosides; D019163:Reducing Agents; C035719:diisobutylaluminum