Carbon tetrabromide → HCID 67508848, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of methyl α-D-glucopyranoside (3.9 g, 20 mmol) in 125 mL of anhydrous pyridine was added triphenylphosphine (10.5 g, 40 mmol) followed by carbon tetrabromide (9.9 g, 30 mmol). The reaction was stirred at 0° C. for 10 minutes then warmed to 65° C. for 4 hours. The reaction was quenched with 20 mL of methanol and concentrated to a crude residue, a portion of which was purified by column chromatography eluting from silica gel with a gradient of 0 to 15% methanol in dichloromethane to give 1.1 g of an off-white solid (64%). 1H NMR (400 MHz, d6-DMSO) δ 3.00-3.06 (m, 1H), 3.16-3.23 (m, 1H), 3.30 (s, 3H), 3.30-3.41 (m, H), 3.47-3.57 (m, 2H), 3.73-3.76 (dd, J=1.6, 10.3 Hz, 1H), 4.56-4.57 (d, J=3.6 Hz, 1H), 4.82-4.83 (d, J=6.4 Hz, 1H), 4.90-4.91 (d, J=5.0 Hz, 1H), 5.21-5.23 (d, J=5.9 Hz, 1H). 13C NMR (100 MHz, d6-DMSO) δ 35.2, 55.0, 71.0, 71.9, 72.3, 73.0, 99.9.

Provenance & Evidence