A convenient route for the synthesis of adenosine

Abstract

A convenient route for the synthesis of adenosine uses hypoxanthine, which is obtained easily and low prices, and phosphorus oxychloride as starting materials was proposed. The route involved three steps as chlorination, condensation and aminolysis, respectively. The reaction condition is mild and the overall yield is higher than other conventional chemical synthesis methods. Firstly, 6-chloropurine was obtained from hypoxanthine and phosphorus oxychloride by chlorination with 90.0% yield. Then, adenosine was produced from 6-chloropurine and tetraacetyl-ribofuranose without separation by condensation and ammonolysis with 75.0% and 66.7% yields, respectively. The total yield of three steps is 45%, the optimum reaction temperature of condensation and ammonolysis are 135 °C and 100 °C, respectiveely. The structures of the compounds were confirmed by TLC, IR, NMR and MS analysis.