Water → HCID 58786153, compound

Participants

Reaction Steps

A 1.0 M THF solution of tetrabutylammonium fluoride (3.8 ml) was added to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-([[t-butyl(diphenyl)silyl]oxy]methyl) phenyl]-D-glucitol (1.7 g) in THF (10.0 ml) at room temperature and the mixture was stirred for two hours. 10% aqueous solution of sodium hydroxide (3.0 ml) was further added to the reaction mixture and the mixture was refluxed with stirring for one hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-(hydroxymethyl)phenyl]-D-glucitol (0.7 g).

Provenance & Evidence