Cesium carbonate → HCID 58786118, compound

Participants

Reaction Conditions

Reaction Steps

Tris(dibenzylideneacetone)dipalladium(0) (17 mg), 2-(dicyclohexylphosphino)biphenyl (22 mg), potassium fluoride (44 mg), and cesium carbonate (247 mg) were added to a solution of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-(bromomethyl) -2-fluorophenyl]-D-glucitol (198 mg) and methyl 2-(tributylstanyl)azulene-1-carboxylate (180 mg) in 1,4-dioxane (10 ml) and the mixture was vigorously stirred at 90° C. for 15 hours. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane). The resulting residue (71 ml) was dissolved in THF-methanol (ratio: 1:1, 6.0 ml). Sodium methoxide (30 mg) was added to the solution and the resulting mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain methyl 2-[2-fluoro-3-[(2S, 3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]benzyl]azulene-1-carboxylate (19 mg).

Provenance & Evidence