[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9](=O)([O:20]C1C=CC([N+]([O-])=O)=CC=1)[O:10][C@@H:11]1[CH2:15][O:14][C@@H:13]2[C@H:16]([OH:19])[CH2:17][O:18][C@H:12]12>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:9](=[O:20])([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[O:10][C@@H:11]1[CH2:15][O:14][C@@H:13]2[C@H:16]([OH:19])[CH2:17][O:18][C@H:12]12To a solution of (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate (1.13 g, 3.63 mmol) in DCM (15 ml), (prepared as described in EXAMPLE 7, Step C), 6-chlorohexanol (596 mg, 4.36 mmol) and 4-dimethylaminopyridine (89 mg, 0.73 mmol) were added and the mixture was stirred at room temperature for 18 hrs. Then the mixture was diluted with DCM and washed with a 5% solution of sodium dihydrogen phosphate (20 ml). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 12 to 80%), affording the title compound as colorless oil.
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