反应详情

A solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (30 g, 77 mmol) in dichloromethane (100 mL) was added 2-fluoroethylamine hydrochloride (8.4 g, 84 mmol) and triethylamine (11.7 mL, 115 mmol). The resulting solution was stirred for 1 hour at room temperature, and then condensed to give a light yellow foam, which was dissolved into dichloromethane (100 mL) and treated with 2,2,2-trifluoroacetic acid (75.6 g, 663 mmol) overnight at room temperature. The reaction mixture was quenched by saturated aqueous sodium carbonate (500 mL), washed with sodium chloride (3×50 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 50% ethyl acetate in petroleum ether to provide compound 66 as a light yellow oil (24 g, 70%). (ES, m/z) [M+H]+ 393.0; 1H NMR (300 MHz, CDCl3) δ 6.27-6.29 (d, J=6.60 Hz, 1H), 5.42-5.44 (1, J=2.7 Hz, 1H), 4.95-4.99 (dd, J=1.8 Hz, 9.5 Hz, 1H), 4.70-4.73 (m, 1H), 4.54-4.65 (m, 1H), 4.37-4.39 (t, J=0.9 Hz, 1H), 4.16-4.17 (m, 2H), 3.81-3.87 (m, 1H), 3.56-3.71 (m, 2H), 2.09 (s, 3H), 2.11 (s, 3H), 2.14 (s, 3H),

1. customcondensed
2. customto give a light yellow foam, which
3. customThe reaction mixture was quenched by saturated aqueous sodium carbonate (500 mL)
4. washwashed with sodium chloride (3×50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under vacuum
7. customto give a residue, which
8. customwas purified by a silica gel column
9. washeluting with 50% ethyl acetate in petroleum ether