Fig. 5 in Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris)

Fig. 5. Synthetic route to AAGs 2 and 2a. I. Acetone, CH3COCl, overnight, room temp. (RT), II. PhCH2Br, K2CO3, DMSO, 50 ̊C, 3.5 h, III. NaOH(aq), TBAB, CHCl3, 50 ̊C, 1 h, IV. Conc. HCl, MeOH, 40 ̊C, 45 min, V. H /Pd–C, MeOH, RT, 3 h, VI. MeONa, MeOH, 20 min, RT, IRA 120 (H +), overall yield 17% (2) and 24% (2a).