Synthesis of novel D-2',3'-dideoxy-2',3'-endo-methylene nucleosides

Article abstract of DOI:10.1016/S0040-4039(97)10531-7

Asymmetric synthesis of D-2',3'-dideoxy-2',3'-endo-methylene nucleosides was achieved via the intermediate 2,3-endo-methylene pentofuranoyl chloride 6, which was prepared from 1,2:5,6-Di-O-isopropylidene-D-mannitol 1 with high stereoselectivity (only α chlorosugar). The SN2 type condensation of 6 with sodium salt of adenine and silyated N⁴-benzoylcytosine gave the desired β-nucleosides as major isomers (β:α = 2.5:1 and 2:1, respectively).