Synthesis of a Novel Bicyclic Nucleoside with a 3,7-Anhydrooctofuranosyl Skeleton

We have developed an efficient route for the synthesis of a novel bicyclic nucleoside using a key intermediate 13, which was prepared from 1,2:5,6-di-O-isopropylidene-α-d-glucose. 1,2-Nucleophilic addition of aldehyde 8 with allyltrimethylsilane and intramolecular Williamson reaction were successfully achieved to synthesize an intermediate with a 3,7-anhydrooctofuranosyl skeleton.