Synthesis Of5’-deoxynucleoside Derivatives

5’-deoxy-nucleosides are potentially interesting medicinal intermediate, since suchmaterials cannot be phosphorylated and incorporated into nucleic acids and thus offer thepossibility of reduced.toxicity and increased specificity. So study on synthesis of5’-deoxy-nucleoside compounds has certain practical significance.In this study, five5’-deoxy-nucleosides including6-chloro-9-(5-deoxy-β-D-ribofuranosyl)-purine,6-amino-9-(5-deoxy-β-D-ribofuranosyl)-purine,6-hydroxy-9-(5-deoxy-β-D-ribofuranosyl)-purine,1-(5-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methylester,1-(5-deoxy-β-D-ribofuranosyl)-4-amino-2-hydroxy-pyrimidinewere synthesized using1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose as the startingmaterial.1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose was synthesized by D-ribose, thereaction process is complex, and the cost of raw material is high. So synthesis of5’-deoxy nucleoside derivatives using inexpensive raw material inosine is considered.Three5’-deoxy-halogenated inosines,6-hydroxy-9-(5-deoxy-chloro-β-D-ribofuranosyl)-purine,6-hydroxy-9-(5-deoxy-bromo-β-D-ribofuranosyl)-purine,6-hydroxy-9-(5-deoxy-iodo-β-D-ribofuranosyl)-purine were synthesized from inosine and halogenating agents. Thedeoxyhalogenation system were respectively acetonitrile/pyridine/SOCl2,Ph3P/pyridine/Br2,Ph3P/pyridine/I2. And then,6-hydroxy-9-(5-deoxy-β-D-ribofuranosyl)-purine was preparedfrom5’-deoxy-halogenated inosines by hydrogenation reduction. The reaction rate of6-hydroxy-9-(5-deoxy-iodo-β-D-ribofuranosyl)-purine was the rapidest of all, and6-hydroxy-9-(5-deoxy-chloro-β-D-ribofuranosyl)-purine can not react. The reduction of6-hydroxy-9-(5-deoxy-chloro-β-D-ribofuranosyl)-purine remains to be studied further.Structures of all intermediates and final compounds were confirmed by IR,1H NMR andMS.