Triphenylphosphine → HCID 86585638, compound

Participants

Reaction Steps

To a solution of 2,3,9,10-tetrafluoro-12-(4-deoxy-4, 4-difluoro-β-D-glucopyranosyl)-6, 7, 12, 13-tetrahydro(5H)indolo[2, 3-a]pyrrolo[3, 4-c]carbazole-5, 7-dione (0.035 g, 0.060 mmol) in 4 mL of dry THF was added triphenylphosphine (0.048 g, 0.18 mmol) and DIAD (0.035 mL, 0.18 mmol), at room temperature under Ar. The resulting reddish-orange solution was stirred at room temperature for 18 h and then it was partitioned with ethyl acetate-water. The organic phase was separated, washed (brine), dried (Na2SO4) and evaporated to give a yellow gum. This residue was purified by prep. tlc (20×20 cm×0.5 mm SiO2/THF-hexane, 1:1) and the major fraction was repurified by prep. hplc to give the title compound (0.009 g, 29%) as a yellow solid: 1H NMR (acetone-d6, 400 MHz) δ 10.67 (s, 1H), 9.83 (s, 1H), 8.88 (m, 1H), 8.73 (m, 1H), 7.56 (m, 2H), 6.44 (m, 1H), 4.91 (m, 2H), 4.47 (d, J=10.0 Hz, 1H), 4.41(d, J=11.0 Hz, 1H), 4.27 (m, 1H); MS (ESI−) m/e 560 (M−H)-; HPLC: 91.1% (320 nm).

Provenance & Evidence