2-Methyl-2-butene → HCID 118377931, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 8a (1.40 g, 1.98 mmol, obtained from the synthetic method described in step 1 of example 8) in tert-butanol (10 mL) were added monopotassium phosphate (2.43 g, 17.82 mmol) and 2-methylbut-2-ene (68.88 mg, 97.02 mmol) at room temperature in turn, and then sodium chlorite (1.26 g, 13.90 mmol) and water (5 mL) were added. The mixture was stirred at 35° C. for 24 hours and quenched with 10 mL of saturated aqueous sodium bicarbonate. Tert-butanol was removed in vavuo. The resulting mixture was extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with saturated aqueous sodium chloride (10 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound 9a as pale yellow oil (1.50 g, 100%). The crude product was used in next step without further purification.

Provenance & Evidence