Synthesis of 3--methyl-D--inositol adenosine analogues

Abstract

Using 3-O-methyl-D-chiro-inositol as starting material, the title compound 5 was synthesized by condensation of adenine and methanesulfonate 3. Additionally, compounds 8 and 9 were prepared through the opening of the epoxide ring in 7 by adenine. The key intermediate 7 was obtained in good yield via an epoxidation from mono-mesylate 6. The process of opening of epoxide ring appeared to be regioselective in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

Keywords

3-O-methyl-D-chiro-inositol / carbocyclic nucleoside analogues / adenine / regioselectivity