Synthesis and Conformational Analysis of 1,5-Anhydro-2,4-dideoxy-D-mannitol Nucleosides

1,5-Anhydro-4,6-O-benzylidene-D-glucitol was used as starting material for the synthesis of 1,5-anhydro-2,4-dideoxy-D-mannitol nucleosides with an adenine and uracil base moiety. The compound with a purine base was obtained by direct nucleophilic substitution of a triflate. The pyrimidine nucleoside could be obtained by epoxide opening followed by inversion of configuration at the 3′-position. Both nucleosides adopt a C1 conformation with an axial base moiety.