Aluminum(III) Chloride → HCID 67074671, compound

Participants

Reaction Steps

To a solution of (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran (12.2 g, 17.9 mmole) in dry DCM (50 mL), AlCl3 (2.8 gm, 21.5 mmole) in diethyl ether was added at 0° C. and stirred at room temperature for 2 hours. The reaction mixture was diluted with water (500 mL) and saturated aqueous NaHCO3 (50 mL), extracted with DCM (2×250 mL). The crude product obtained after the removal of solvent was purified using silica gel column chromatography (10% ethyl acetate in hexane) to furnish 6.1 g of {(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-tetrahydro-pyran-2-yl}-methanol.

Provenance & Evidence