Fig. 3. Synthesis of alternative 1-deoxy-ribose ILs with varying 2- and 3-O-groups. (a) 2,2-Dimethoxy propane, camphorsulfonic acid, acetone, r.t., 1.5 h; (b) Tf2O, pyridine, DCM, 0 °C, 10 min; (c) pyridine, reaction at rotary evaporator, 700 mbar, 40 °C; (d) AcOH (70%), r.t., 20 min; (e) NaH, ethyl or allyl bromide, DMF, 0 °C ≥ r.t., overnight; (f) AcOH (70%), 70 °C, 45 min; (g) Pd(OH)2, MeOH, H2-atmosphere, r.t., 12 h; (h) Tf2O, pyridine, DCM, 0 °C, 10 min; (i) pyridine, reaction at rotary evaporator, 700 mbar, 40 °C; *yield over two steps.
