title: Substitution effect of purine nucleosides on diisobutylaluminum hybride reduction.
abstract: 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.
authors.affiliation: Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Hirota
authors.forename: Y
authors.initials: Y
authors.lastname: Monguchi
authors.forename: M
authors.initials: M
authors.lastname: Sako
authors.forename: Y
authors.initials: Y
authors.lastname: Kitade
mesh_terms: 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*
chemical_list: D009942:Organometallic Compounds; D011684:Purine Nucleosides; D019163:Reducing Agents; C035719:diisobutylaluminum