HCID 14621461, compound → HCID 14621463, compound

Participants

Reaction Steps

A solution of (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5-ethoxycarbonylmethyl-2-methyl-1,3-dioxane (9.30 g) in toluene (93 ml) was cooled in a dry ice acetone bath and to the solution was added dropwise diisobutyl aluminum hydride (1.5 M solution in toluene, 26.4 ml). The mixture was stirred at the same temperature for 1 hour. After quenching the mixture with saturated aqueous ammonium chloride, to the solution was added a mixture of ethyl acetate (300 ml) and water (300 ml). Insoluble materials were filtered off. The filtrate was extracted with ethyl acetate and organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (250 g) with a mixture of n-hexane and ethyl acetate (10:1) as an eluent to give (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5-formylmethyl -2-methyl-1,3-dioxane (6.61 g) as a colorless oil.

Provenance & Evidence