P([O-])([O-])([O-])=O.[CH2:6]([N:9]1[CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][O:11][S@@:10]1=[O:17])[CH2:7][CH3:8].I([O-])(=O)(=O)=[O:19].[Na+]>C(OCC)(=O)C.O.[Ru](=O)=O>[CH2:6]([N:9]1[C@@H:13]([CH2:14][CH2:15][CH3:16])[CH2:12][O:11][S:10]1(=[O:19])=[O:17])[CH2:7][CH3:8]Ruthenium dioxide hydrate (3 mg) and a phosphate buffer solution (pH 7.4, 28.7 mL) were subsequently added to a solution of (S)-3,4-dipropyl-1,2,3-oxathiazolidine 2-oxide (5.74 g) in ethyl acetate (46 mL) under ice-cooling and stirring. Sodium periodate (7.06 g) was added to the solution under ice-cooling and stirring, and then vigorously stirred at room temperature for 30 minutes. The suspension was filtered, and the insoluble matter was washed with ethyl acetate (17 mL). The filtrate and the washings were combined. The organic layer was separated and washed subsequently with a saturated aqueous sodium hydrogen carbonate solution (11.5 mL), an aqueous 10% sodium thiosulfate solution (11.5 mL) and a saturated aqueous sodium chloride solution (11.5 mL). Anhydrous sodium sulfate and activated carbon (0.57 g) were added to the organic layer and stirred at room temperature for 1 hour. The suspension was filtered, and the filtrate was concentrated under reduced pressure. The residue was added with tetrahydrofuran (8.6 mL) and concentrated under reduced pressure at 40° C. or lower to give (S)-3,4-dipropyl-1,2,3-oxathiazolidine 2,2-dioxide (5.83 g, 94% yield) as an orange-brown oil.
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