反应详情

To a solution of 12-[4-deoxy-2,3,6-tri-O-benzyl-β-D-glucopyranosyl]-2,3,9,10-tetrafluoro-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (6.49 g, 7.97 mmol) in 90 mL of acetic anhydride was added solid I2 (0.406 g, 1.6 mmol) and the mixture was stirred at room temperature for 16 h. The resulting mixture was diluted with ethyl acetate, washed (30% aq. Na2S2O3, saturated aq. NaHCO3, H2O, brine) dried (MgSO4) and evaporated. The residue was taken up in methanol (150 mL), 15 mL of concentrated NH4OH was added and the mixture was stirred at room temperature for 18 h. The mixture was then evaporated to dryness and the residue was chromatographed (SiO2/hexane-ethyl acetate, 95:5 to 1:1) to give 12-[4-deoxy-2,3,-di-O-benzyl-β-D-glucopyranosyl]-2,3,9,10-tetrafluoro-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (2.35 g, 41%) and then 12-[4 deoxy-2-O-benzyl-β-D-glucopyranosyl]-2,3,9,10-tetrafluoro-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (2.40 g, 48%), both as yellow solids.

1. washwashed (30% aq. Na2S2O3, saturated aq. NaHCO3, H2O, brine)
2. dry with materialdried (MgSO4)
3. customevaporated
4. addition15 mL of concentrated NH4OH was added
5. stirringthe mixture was stirred at room temperature for 18 h
6. customThe mixture was then evaporated to dryness
7. customthe residue was chromatographed (SiO2/hexane-ethyl acetate, 95:5 to 1:1)