Benzyl Bromide → HCID 67075027, compound

Participants

Reaction Steps

To a solution of (2S,3R,4R,5S)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methylene-tetrahydro-pyran-3,4,5-triol (300 mg, 0.77 mmole) in dry DMF (3 mL), sodium hydride (166 mg, 3.46 mmole) was added at 0° C. and stirred at room temperature for 2 hours. Benzyl bromide (0.3 mL, 2.54 mmole), t-butylammoniumiodide (10 mg) was added and reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with water (50 mL) and extracted with DCM (2×200 mL). The crude product was purified by silica gel column chromatography (2% ethylacetate in hexane) to furnish 300 mg of (2S,3S,4R,5S)-3,4,5-tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methylene-tetrahydro-pyran.

Provenance & Evidence