Acetone → 4-(Hydroxymethyl)phenyl-alpha-D-galactopyranoside tetraacetate

HRID 863780Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@@H:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][C@@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].CC(C)=[O:35]>[N+]([O-])([O-])=O.[Ag+]>[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@@H:17]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[O:16][C@@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:35])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1.89 g of the compound 2 in 80 ml of acetone is mixed with an equal volume of a 0.1N aqueous solution of silver nitrate. The mixture is stirred at 25° C. for 2 h, the acetone is then evaporated off under reduced pressure, the remaining aqueous phase is extracted with CH2Cl2 and the extract is washed with water and then dried over anhydrous sodium sulfate, filtered and evaporated to dryness under reduced pressure. The dry residue obtained (1.52 g) is then purified by flash chromatography on a column of silica (solvent: hexane/ethyl acetate: 60/40 v/v). The product 4 (0.94 g) is obtained with a yield of 56%.

Workup

customthe acetone is then evaporated off under reduced pressure
extractionthe remaining aqueous phase is extracted with CH2Cl2
washthe extract is washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated to dryness under reduced pressure
customThe dry residue obtained (1.52 g)
customis then purified by flash chromatography on a column of silica (solvent: hexane/ethyl acetate: 60/40 v/v)

Sources & evidence

ORD record: ord-bab7c0ef892342cfbe9676069e15dad2
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05561119

Reaction notes

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