[CH3:1][C@@H:2]1[O:6][S:5](=[O:7])[N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.I([O-])(=O)(=O)=[O:16].[Na+]>C(#N)C.O.C(OCC)(=O)C>[CH3:1][C@@H:2]1[O:6][S:5](=[O:16])(=[O:7])[N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3]1To a solution of tert-butyl (5S)-5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide (5.7 g, 25.8 mmol) in acetonitrile (60 mL) and water (30 mL) is added sodium periodate (8.3 g, 38.7 mmol) in one portion. After 5 min, a few crystals of RuCl3 is added. The reaction is stirred for 3 h and the resulting thick slurry is diluted with water (100 mL) and ethyl acetate (20 mL) and is passed through a bed of Celite, rinsing with additional EtOAc. The filtrate is concentrated to remove the organic solvents and the resulting solid is isolated by filtration to afford the title compound (6.0 g, 97%).
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