Formaldehyde → (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde

Participants

Reaction Steps

To a solution of (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 25i (1.0 g, 1.3 mmol) in N,N-dimethyl formamide (20 mL) was added formaldehyde (2.6 mL, 32.5 mmol, 37 wt % solution) at room temperature, and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.3 mL, 0.78 mmol) was added to adjust the pH to 9. The mixture was stirred at room temperature for 16 hours and extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with water (30 mL×2) and saturated aqueous sodium chloride (30 mL×2) in turn, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 25j as yellow oil (1.04 g, 100%). This material was not further purified.

Provenance & Evidence