[N+:1]([O-:4])([OH:3])=[O:2].C(OC(=O)C)(=O)C.[CH2:12]1[O:16][C@@H:15]2[C@H:17]([OH:20])[CH2:18][O:19][C@@H:14]2[C@@H:13]1O>C(Cl)Cl>[N+:1]([O-:4])([O:3][C@@H:13]1[CH2:12][O:16][C@@H:15]2[C@H:17]([OH:20])[CH2:18][O:19][C@H:14]12)=[O:2]To a solution of fuming nitric acid (0.92 mL, 22.2 mmol) in CH2Cl2 (44 mL) and acetic anhydride (2.10 mL, 22.2 mmol) cooled to −20° C., 1,4:3,6-dianhydro-D-mannitol (2.50 g, 17.1 mmol) was added as solid. After the reaction mixture was stirred at 0° C. for 3 hours, it was slowly poured into ice/NaHCO3. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by flash chromatography (Biotage SP1, column SNAP 100, EtOAc/n-hexane from 30 to 100%), affording the title product as a white solid (1.35 g, yield 41%). 1H-NMR (300 MHz, CDCl3); δ 5.39 (1H, q), 4.89 (1H, t), 4.49 (1H, t), 4.35-4.27 (1H, m), 4.10-4.04 (2H, m), 3.58 (2H, t), 2.40 (1H, d).
Wird geladen…
