Synthesis of (±)-c-4-amino-r-1,t-2,c-3-cyclopentanetrimethanol and higher homologues of 8-azapurine arabino-carbocyclic nucleosides

(±)-c-4-Amino-r-1,t-2,c-3-cyclopentanetrimethanol () was synthesized from previously reported (±)-c-4,t-5-bis(benzoyloxymethyl)-r-1,c-3-cyclopentanedicarboxylic anhydride by methanolysis (which selectively esterified the less hindered carboxyl), oxidative degradation of the other to an amino group, and DIBAL-H reduction. Amino alcohol was then converted into (±)-c-4-[(5-amino-6-chloropyrimidin-4-yl)amino]-r-1,t-2,c-3-cyclopentanetrimethanol, which was used for synthesis of 8-azapurine arabino-carbocyclic nucleoside analogues. Two N,N′-dicyclopentanylurea derivatives obtained as side products of the synthesis of are also described.