Novel carbohydrate-derived spirodifluorocyclopropane analogues as possible radical and ionic probes have been synthesized. Treatment of 3-methylene sugar 1, derived from diacetone glucose, with difluorocarbene generated in situ from acid free trimethylsilyl fluorosulfonyldifluoroacetate reagent (TFDA; NaF/benzene/80 ^oC/3 h) produced spirodifluorocyclopropane as a 2:1 mixture of two isomers. The difluorocarbene reagent presumably added preferentially from the less hindered β-face to give 2 as major product. Difluorocyclopropylation of the ribose derivative having exomethylene group at C2 next to anomeric carbon with TFDA produced 3 (8:1; 45%, ¹⁹F NMR). Attempts to synthesize other spirodifluorocyclopropane sugar and nucleoside analogues will be also discussed.