Chloride → HCID 52914724, compound

Participants

Reaction Steps

To a solution of oxallyl chloride (0.05 mL, 0.72 mmole) in dry DCM (5 mL), DMSO (0.1 mL, 1.43 mmole) in DCM (1 mL) was added at −70° C. and stirred for 10 min., Solution of {(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-tetrahydro-pyran-2-yl}-methanol (500 mg, 0.72 mmole) in DCM (4 mL) was added during 15 min at −70° C. and the reaction mixture stirred for 1 hour. Triethylamine (0.5 mL, 3.5 mmole) was added and allowed to stir at room temperature for 15 min. The reaction mixture was diluted with water (25 mL) and extracted with DCM (2×25 mL). The combined organic layer washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL), The crude product obtained after the removal of solvent was co evaporated with toluene (20×4) to furnish crude aldehyde. To this crude aldehyde 1-4 dioxane (10 mL), 1N NaOH (2 mL), 37% aq. HCHO (2 mL) were added and stirred for 72 hours at room temperature. The reaction mixture was diluted with water (25 mL) and neutralized with 1N HCl, extracted with ethyl acetate (2×25 mL). The crude product obtained after the removal of solvent was purified using silica gel column chromatography (20% ethyl acetate in hexane) to furnish 210 mg of {(3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol

Provenance & Evidence