Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis

Article abstract of DOI:10.1016/S0040-4020(99)00287-2

D-Altritol nucleosides with an adenine and uracil base moiety were obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro- 4,6-O-benzylidene-D-allitol using the sodium salt of the above mentioned bases. The use of a 2-trimethylsilylethyl protecting group for the O⁶- function of the guanine base offers a useful compromise between stability and acceptable alkylation yields of the N⁹-position if the guanine base. The cytosine nucleoside was synthesized starting from the uracil congener. The 3'-hydroxyl function was protected with a benzoyl group.