反应详情

To a stirred solution of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (intermediate D1) (37 mg, 0.097 mmol) in 1.5 ml of DMF was added Cs2CO3 (48 mg, 0.146 mmol) and (E)-(3-bromoprop-1-enyl)cyclopropane (intermediate BY) (50 mg) at room temperature. After stirring for 3 h, the reaction was quenched with 2 ml of ice water. The mixture was extracted 3× with ethyl acetate (5 ml), and the combined organic layers were washed 2× with water (5 ml) and brine, dried over Na2SO4, concentrated, and purified by preparative LC-MS to obtain compound BZ (8.6 mg). 1H NMR (CD3OD, 400 MHz): δ 7.37˜7.33 (2H, m), 7.30˜7.27 (1H, dd, J=8.2, 2 Hz), 7.11˜7.09 (2H, d,J=8.8 Hz), 6.82˜6.79 (2H, d,J=8.8 Hz), 5.77˜5.70 (1H, dt, J=15.2, 6 Hz), 5.39˜5.33 (1H, dd, J=15.2, 8.8 Hz), 4.43˜4.41 (2H, dd, J=6.4, 1.0 Hz), 4.10 (1H, d, J=9.6 Hz), 4.08˜3.98 (2H, dd,J=23.6, 15.2 Hz), 3.90˜3.87 (1H, m), 3.72˜3.67 (1H, m), 3.49˜3.39 (3H, m), 3.31˜3.27 (1H, m), 1.47˜1.45 (1H, m), 0.76˜0.71 (2H, m), 0.41˜0.37 (2H, m); MS ESI (m/z) 461 (M+H)+, calc. 460.

1. customthe reaction was quenched with 2 ml of ice water
2. extractionThe mixture was extracted 3× with ethyl acetate (5 ml)
3. washthe combined organic layers were washed 2× with water (5 ml) and brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. custompurified by preparative LC-MS
7. customto obtain compound BZ (8.6 mg)