Iodine → HCID 20758621, compound

Participants

Reaction Steps

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.

Provenance & Evidence