Methanol → 3-O-(2,3,4-tri-O-benzyl-6-thio acetyl-alpha-D-quinovopyranosyl)-1-O-stearoyl-propane-1,3-diol

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Reaction Steps

To a solution of the compound (7) (21.9 g, 38.6 mmol) in anhydrous dichloromethane (200 ml), added were stearoyl chloride (15.2 g, 1.3 equivalents) and anhydrous pyridine (5 ml), and the mixture was stirred at room temperature for 2 hours. After the sufficient progress of the reaction was confirmed, methanol (5 ml) was added to stop the reaction, and the mixture was concentrated under reduced pressure. The residue was suspended in a minor amount of ethyl acetate, poured to water (200 ml), and extracted with ethyl acetate (3×100 ml). The organic layers were combined and washed with saturated saline (2×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 10:1→8:1→6:1) to obtain the title compound (8) in the form of a colorless oily substance {31.3 g (37.6 mmol), 97.4%}.

Provenance & Evidence