Toluene → HCID 67304246, compound

Participants

Reaction Steps

To a tetrahydrofuran solution (2.0 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-chloro-5-[4-(2-hydroxyethyl)benzyl]phenyl]-D-glucitol (79.0 mg, 0.090 mmol), triphenyl phosphine (53.1 mg, 0.203 mmol), and phthalimide (23.9 mg, 0.162 mmol) cooled in ice was added a 40% diisopropyl azodicarboxylate solution in toluene (386 μL, 0.203 mmol) under nitrogen atmosphere. After the reaction solution was stirred at room temperature for 1.5 hours, methanol (1 mL) was added thereto. Then hydrazine monohydrate (43.7 μL, 0.90 mmol) was added, and the reaction mixture was stirred at 60° C. for 3 hours. After the mixture was cooled to room temperature, a 2 M sodium hydroxide aqueous solution was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=9:1) to obtain the title compound (39.2 mg, 50%) as a colorless oily compound.

Provenance & Evidence