Benzyl Bromide → 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

HRID 397234Notes

Reaction equation

[C@H:1]1([F:12])[O:9][C@H:8]([CH2:10][OH:11])[C@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[Ag]=O>[CH2:13]([O:3][C@@H:2]1[C@@H:4]([O:5][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:6]([O:7][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:8]([CH2:10][O:11][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:9][C@@H:1]1[F:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -20 °C

Procedure

α-D-galactopyranosyl fluoride (2.30 g, 12.62 mmol) was dissolved in dry DMF (40 ml) and, at −20° C., benzyl bromide (12.95 g, 75.72 mmol) and silver oxide (10 g) were added. The reaction mixture was stirred at −20° C. for 5 h and then at room temperature for 24 h. The salts were then filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (350 g) with 15:1 petroleum ether/ethyl acetate.

Workup

waitat room temperature for 24 h
filtrationThe salts were then filtered off
customthe filtrate was evaporated in vacuo
customThe residue was purified by column chromatography on silica gel (350 g) with 15:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record: ord-b2da0d3aa729451dbbaa72e8562eabfb
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610299B1

Reaction notes

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