反应详情

温度

60 °C

Acetonide 31 made as described above, (209 mg, 1.12 mmol) was dissolved in a mixture of AcOH/THF/H2O (2:1:1, 3 mL). The solution was stirred at 60° C. for 6 h. The solvent was evaporated and 164 mg (1.1 mmol, 99% yield) of Conduritol F was obtained. An analytical sample was obtained after recrystallization from MeOH-ether. Rf =0.18 (CHCl3 --MeOH, 4:1); mp=131°-132° C. (lit* 129°-130° C.); [α]20D =-84 (c 0.71, MeOH) (lit.* -70.5°, MeOH); IR (KBr) υ 3283, 2920, 1420, 1102, 1061 cm-1 ; 1H NMR (CDCl3) δ 5.79 (1H, ddd, J=10.0, 4.7, 1.9 Hz), 5.71 (1H, dd, J=10.0, 1.9 Hz), 4.15 (1H, t, J=4.3 Hz), 3.92 (1H, dt, J=7.5, 1.6 Hz), 3.61 (1H, dd, J=10.4, 7.7 Hz), 3.41 (1H, dd, J=10.4, 4.2 Hz); 13C NMR (CDCl3) δ 133.8 (CH), 128.1 (CH), 74.1 (CH), 73.8 (CH), 72.7 (CH), 68.0 (CH); MS (El) m/z (rel. intensity) 128 (8), 110 (11), 99 (98), 86 (100); Anal. Calcd for C6H10O4 : C, 49.31; H, 6.90; Found: C, 49.30; H, 6.94.

1. customThe solvent was evaporated