Fig. 2. Synthesis of 1-deoxy-ribose based ionic liquid 1i; the same synthetic strategy was applied for lyxose (2a–i), xylose (3a–i) and arabinose (4a–i). (a) Thiophenol, BF₃·OEt₂, DCM, 0 °C ≥ r.t., 2 h; (b) Bu₃SnH, AIBN, toluene, reflux, 2.5 h; (c) MeOH, Na, r.t., 4 h; (d) trityl chloride, NEt₃, DMAP, DCM, r.t., overnight; (e) NaH, MeI, DMF, 0 °C ≥ r.t., overnight; (f) AcOH (70%), 70 °C, 45 min; (g) Tf₂O, pyridine, DCM, 0 °C, 10 min; (h) pyridine, reaction at rotary evaporator, 700 mbar, 40 °C; *yield over two steps.