[C@@H:1]12[O:6][C@@H:5]1[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]2.[OH2:11].[Na+].[Cl-]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[OH:6][C@H:1]1[C@H:5]([OH:11])[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1Methyl (1S,5R)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (8 g, 56.3 mmol) and tetrabutylammonium bisulfate (1.911 g, 5.63 mmol) were suspended in THF (5 ml) and water (75 ml) and allowed to stir for 48 hrs. Added solid NaCl and extracted with three 250 ml portions of EtOAc. Added 100 ml Hexane washed with brine and dryed over sodium sulfate. Silca gel chromatography on a 50 g Biotage SNAP cartridge with 40-60% acetone-hexane to give title product as a clear oil. 1H NMR (500 MHz, CDCl3) δ 1.89-2.03 (m, 3H), δ 2.26-2.42 (m, 3H), δ 3.08-3.15 (m, 1H), δ 3.74 (s, 3H), δ 4.06 (m, 1H), δ 4.23 (m, 1H)
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