Imidazole → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Participants

Reaction Steps

To a solution of the crude acetyl glucal 3 (12.5 g, 45.9 mmol) in dry MeOH (150 mL) was added a solution of sodium methoxide (NaOMe, 4.59 mmol) in dry MeOH (1 mL) at room temperature. The reaction mixture was stirred for 30 min and evaporated to dryness. The residue was dissolved in dry N,N-dimethylformamide (DMF, 150 mL) at 0° C. and to this solution was added imidazole (9.4 g, 137.7 mmol) and tert-butyldimethylsilyl chloride (10.4 g, 68.9 mmol). The reaction mixture was stirred for 3 h at room temperature, diluted with icewater, and extracted with 50% ethyl acetate (AcOEt)-hexane. The organic extract was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel (200 g) using 50% AcOEt-hexane to yield 4 (7.15 g, 65% from D-glucose).

Provenance & Evidence