Potassium Phosphate, Tribasic → HCID 86691700, compound

Participants

Reaction Conditions

Reaction Steps

Step-IX: To a stirred solution of acetic acid (3S,4R,5S,6S)-3,4,5-triacetoxy-6-[4-bromo-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2-yl ester (2.75 g, 4.4 mmol) in toluene (25 ml) was added tricyclohexylphosphine (495 mg, 1.8 mmol), a solution of potassium phosphate tribasic (3.75 g, 1.8 mmol) in water (5 ml), cyclopropylboronic acid (1.14 g, 13.2 mmol). The reaction mixture was degassed for 45 min then added palladium (II) acetate (148 mg, 0.7 mmol). Reaction mixture was stirred at 90° C. for overnight. Reaction mixture was cooled to room temperature and was filtered through celite bed, washed with ethyl acetate (25 ml). Organic layer was washed with water (25 ml) followed by brine (25 ml), dried over sodium sulfate, concentrated and purified by column chromatography to give 1.9 g of acetic acid (3S,4R,5S,6S)-3,4,5-triacetoxy-6-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2-yl ester. MS (ES) m/z 600.3 (M+18).

Provenance & Evidence