Sodium Iodide → HCID 86622033, compound

Participants

Reaction Steps

To a solution of 4-[2-(4-benzyloxyphenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine (0.43 g) in acetone (7 mL) were added cesium carbonate (0.33 g), methyl 2-bromoacetate (0.072 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-3/2) to give 4-[2-(4-benzyloxy-phenyl)ethyl]-1-methoxycarbonylmethyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine (0.42 g). This material was dissolved in a mixed solvent of methanol (10 mL) and tetrahydrofuran (5 mL). To the solution was added sodium methoxide (28% methanol solution, 0.3 mL), and the mixture was stirred at 55° C. for 4 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added 2 mol/L aqueous sodium hydroxide solution (15 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2 mol/L hydrochloric acid (17 mL), and the mixture was stirred at room temperature for 30 minutes. The mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound (0.16 g).

Provenance & Evidence