反应详情

To ((1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′-trihydroxy-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-6′-yl)methyl 4-methylbenzenesulfonate (14 mg, 0.024 mmol) was added 1 mL of freshly prepared sodium trifluoroethoxide solution (1.5 M). After refluxing for 5 h at temperature, the reaction was quenched with 2 mL of water. The organic solvent was distilled off and the water layer was extracted with ethyl acetate. The combined organic layers were washed with brine prior to drying over Na2SO4. Concentration under reduced pressure provided the crude product, which was purified by preparative TLC to give 6 mg of title compound. 1H NMR (CD3OD, 300 MHz) δ 7.36 (s, 1H), 7.19 (s, 1H), 7.09 (s, 4H), 5.12 (d, J=13.2 Hz, 1H), 5.07 (d, J=13.2 Hz, 1H), 4.11 (d, J=15.5 Hz, 1H), 4.05 (d, J=15.5 Hz, 1H), 3.89-3.66 (m, 7H), 3.48 (t, J=9.2 Hz, 1H), 2.59 (q, J=7.8 Hz, 2H), 1.19 (t, J=7.8 Hz, 3H); MS ESI (m/z) 503 (M+1)+, calc. 502.

1. temperatureAfter refluxing for 5 h at temperature
2. customthe reaction was quenched with 2 mL of water
3. distillationThe organic solvent was distilled off
4. extractionthe water layer was extracted with ethyl acetate
5. washThe combined organic layers were washed with brine
6. dry with materialto drying over Na2SO4
7. concentrationConcentration under reduced pressure
8. customprovided the crude product, which
9. customwas purified by preparative TLC