CC1(C)[O:6][CH:5]([C@H:7]2[O:16][C@@H:10]3[O:11][C:12]([CH3:15])([CH3:14])[O:13][C@@H:9]3[CH2:8]2)[CH2:4][O:3]1.C([O-])(O)=O.[Na+]>CC(O)=O.O>[CH3:14][C:12]1([CH3:15])[O:11][C@H:10]2[O:16][C@H:7]([C@@H:5]([OH:6])[CH2:4][OH:3])[CH2:8][C@H:9]2[O:13]1A solution of (3aR,5S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole (compound 1b, 10.0 g, 40.9 mmol) in 60% HOAc in water (20 mL) was stirred at 40° C. for 16 hours. The reaction mixture was adjusted to pH 8˜8.5 by saturated NaHCO3 solution and extracted with EtOAc. The organic layer was combined and concentrated, the residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether) to afford 5.2 g of (1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (compound 1c). MS obsd. (ESI+) [(M+NH4)+]: 222.
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