Stereoselective Synthesis of 3′-Fluoro- and 3′-Azido-4′-methyl-2′,3′-D-glycero-pentofuranoside-5-fluorouracils.

Abstract Total stereoselective synthesis of 2,3-dideoxy-3-fluoro- and 2,3-dideoxy-3-azido- d - glycero -pentose and their condensation with 5-fluorouracil is described. The key step in this synthesis is nucleophilic cleavage of a chiral epoxyalcohol, prepared from commercially available 2-methyl-2-butenal.