Facile reductive cleavage of purine nucleosides to acyclonucleosides using diisobutylaluminium hydride (DIBAL): a new synthetic method for the preparation of 9-ribitylpurine derivatives.
Reaction of purine nucleosides, such as 2',3'-isopropylideneinosine (1a) and 2',3'-isopropylideneadenosine (1c), with diisobutylaluminum hydride (DIBAL) in dry tetrahydrofurane resulted in the formation of the corresponding 9-(2',3'-isopropylideneribity)purines (2) in good yields. Oxidation of the ribityl derivatives (2) with NalO4 and subsequent reduction with NaBH4 gave the corresponding 9-(2',3',4'-trihydroxybutyl)-purine derivatives (4) in high yields. Deprotection of compounds 2 and 4 in 80% acetic acid gave the corresponding 9-(2',3',4'-trihydroxybutyl)purines (5) and 9-ribitylpurines (6), respectively.
Kitade
Y
Y
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi, Japan.
Hirota
K
K
Maki
Y
Y
D007202:Indicators and Reagents; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011684:Purine Nucleosides / Q000737:chemistry*; D012263:Ribonucleosides / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D009942:Organometallic Compounds; D011684:Purine Nucleosides; D012263:Ribonucleosides; C035719:diisobutylaluminum