HCID 10989032, compound → HCID 11096141, compound

Participants

Reaction Steps

A solution of 109 (5.4 g, 20.1 mmol) in 30% aqueous AcOH (150 mL) was stirred at room temperature for 50 h. The reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) to give the diol 110 (3.4 g, 75%) as a syrup: 1H NMR (CDCl3) δ 1.34 (s, 3H, CH3), 1.53 (s, 3H, CH3), 2.90 (dd, 1H, J=12.9, 2.2 Hz, 6′-CHH), 3.09 (dd, 1H, J=12.9, 4.8 Hz, 6′-CHH), 3.27 (dd, 1H, J=7.8, 1.9 Hz, 4′-H), 3.49 (br s, 2H, 2×OH), 3.58–3.72 (m, 2H, HOCHHCH(OH)), 3.79 (dd, 1H, J=11.0, 2.9 Hz, HOCHH), 4.93 (m, 2H, 3a-H, 6a-H); Anal. Calcd for C19H16O4S: C, 49.07; H, 7.32; S, 14.56 . Found: C, 49.24; H, 7.72; S, 14.23.

Provenance & Evidence