Chloride → HCID 52914724, compound

Participants

Reaction Steps

To a solution of oxallyl chloride (0.05 mL, 0.718 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, 0.718 mmole) in DCM (4 mL) was added during 15 min at −70° C. and reaction mixture stirred for 1 hour. Triethylamine (0.5 mL, 3.5 mmole) was added and allowed stir at room temperature for 15 min. The reaction mixture was diluted with water (25 mL) and the organic layer washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL), extracted with DCM (2×25 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. formaldehyde (2 mL) were added and stirred for 72 hours at room temperature. The reaction mixture was diluted with water (25 mL) and washed with 1N HCl (15 mL), 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