Water → 1-O-(2,3,4-tri-O-benzyl-6-thioacetyl-alpha-D-quinovopyranosyl)-propane-1,3-diol

Participants

Reaction Conditions

Reaction Steps

To a solution of the compound (6) (28.2 g, 42.5 mmol) in anhydrous DMF (300 ml), added was potassium thioacetate (7.28 g, 1.5 equivalents), and the mixture was stirred at 90° C. for 3 hours. After the sufficient progress of the reaction was confirmed, the reaction liquid was poured to chilled water (900 ml), extracted with ethyl acetate (3×300 ml). The organic layers were combined and washed with saturated saline (2×200 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 2:1→3:2→1:1→2:3) to obtain the title compound (7) in the form of light brown oily substance {21.9 g (38.6 mmol), 90.8%}.

Provenance & Evidence