Carbon tetrabromide → HCID 67508848, compound

HRID 1770721Notes

Reaction equation

[O:1]([CH3:13])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>N1C=CC=CC=1>[Br:34][CH:11]([OH:12])[C@H:9]1[O:10][C@H:2]([O:1][CH3:13])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperaturethen warmed to 65° C. for 4 hours
customThe reaction was quenched with 20 mL of methanol
concentrationconcentrated to a crude residue
customa portion of which was purified by column chromatography
washeluting from silica gel with a gradient of 0 to 15% methanol in dichloromethane

Sources & evidence

ORD record: ord-5266a8ece57b42be987e2a56ed094713
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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