Sodium borohydride → HCID 68015203, compound

Participants

Reaction Steps

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 4k (7.9 g, 10.45 mmol) was dissolved in 50 mL of mixed solution (THF and MeOH, v:v=2:3), followed by addition of sodium borohydride (794 mg, 20.9 mmol). The reaction mixture was stirred for 30 minutes. Thereafter, the reaction mixture was concentrated under reduced pressure after a small amount of acetone was added and the resulting residue was purified by silica gel chromatography with elution system A to obtain the title compound [(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 4m (1.11 g, colourless grease), yield: 14.1%.

Provenance & Evidence