Formaldehyde → HCID 86685161, compound

Participants

Reaction Conditions

Reaction Steps

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 9h (1.53 g, 2.1 mmol) was dissolved in 15 mL 1,4-dioxane, followed by addition of 3.4 mL 37% formaldehyde solution and 6.3 mL 1 M sodium hydroxide. The reaction mixture was stirred for 16 hour at 70° C., and was partitioned after 50 mL saturated sodium chloride solution were added. The aqueous phase was extracted with ethyl acetate (50 mL×3) and the organic extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 91 (2.0 g, pale yellow grease), which was used directly in the next step without purification.

Provenance & Evidence