Benzoyl Peroxide → HCID 86755268, compound

Participants

Reaction Steps

N-bromosuccinimide (117.2 mg, 0.66 mmol) and benzoyl peroxide (159 mg, 0.66 mmol) were added to a solution of methyl 1-(2-nitro-4-methylphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (206 mg, 0.44 mmol) in carbon tetrachloride (20 ml). The mixture was refluxed for 5 hours and stirred at room temperature for 12 hours. The reaction mixture was evaporated under reduced pressure, and purified by column chromatography on silica gel (ethyl acetate-hexane, 2:3) to give 47 mg of methyl 1-(2-nitro-4-bromomethylene-phenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate in 20% yield. 1H NMR (300 MHz, DMSO-d6) δ1.98-2.02 (m, 9H, CH3), 3.64 (s, 3H, OCH3), 4.73 (s, 2H, CH2), 4.77 (s, 1H, sugar-H), 5.09-5.13 (m, 2H, sugar-H), 5.47 (t, J=9 Hz, 1H, sugar-H), 5.76 (d, J=7.7 Hz, 1H, sugar-H), 7.43 (d, J=8.7 Hz, 1H, ArH), 7.76 (d, J=8.7 Hz, 1H, ArH), 8.02 (s, 1H, ArH).

Provenance & Evidence