Potassium chromate(VI) → HCID 59557758, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (10 g, 10.8 mmol) (prepared using methods analogous to those described in US20040138439) in acetic acid (130 mL) at 120° C. was added potassium chromate (6.3 g, 21.4 mmol) in one portion. The mixture was stirred for 22 hours at 120° C. The solvents were removed under reduced pressure, ethyl acetate was added, and the solid was filtered. The organic layer was washed with saturated aqueous sodium bicarbonate and then with brine, and then dried over sodium sulfate. The sample was concentrated, and the resulting residue was purified by silica gel chromatography (3:1 petroleum ether:ethyl acetate) to give pure product 47 as a solid (2.3 g). 1H-NMR (CDCl3, 400 MHz): δ 7.90 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.4 Hz, 1H), 7.26 (d, J=8.4 Hz, 2H), 7.22 (dd, J=8.4, 2.2 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H), 5.31 (t, J=9.4 Hz, 1H), 5.22 (t, J=9.8 Hz, 1H), 5.09 (t, J=9.4 Hz, 1H), 4.35 (d, J=10.0 Hz, 1H), 4.29 (dd, J=12.4, 4.8 Hz, 1H), 4.18-4.13 (m, 3H), 3.85-3.81 (m, 1H), 2.60 (s, 3H), 2.09 (s, 3H), 2.07 (s, 3H), 2.01 (s, 3H), 1.75 (s, 3H); MS ESI: 575 [M+H]+, 619 [M+HCO2]−.

Provenance & Evidence