Methanesulfonic Acid → (2S,3R,4S,5S,6R)-2-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

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Reaction Steps

To a solution of (2S,3R,4S,5R,6R)-2-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl)phenyl]methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol 17d (45.0 g, 58.0 mmol) in anhydrous methanol (120 mL) was added methylsulfonic acid (11.3 mL, 174 mmol). The mixture was stirred at room temperature for 16 hours. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate till pH becomes 7 and concentrated in vacuo to remove most of the solvent. The residue was partitioned between water (200 mL) and ethyl acetate (200 mL). The aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with saturated aqueous sodium chloride (200 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by re-crystallization from a toluene/n-hexane mixture (v/v)=1/1 to give the title compound 17e as yellow solid powder (12.5 g, 54.3%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 537.1 [M+HCOO]−.

Provenance & Evidence