Methanesulfonic Acid → HCID 118377808, compound

Participants

Reaction Steps

To a solution of (2S,3R,4S,5R,6R)-2-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol 25d in anhydrous tetrahydrofuran was added a solution of methylsulfonic acid (0.2 mL, 2.82 mmol) in methanol (20 mL) at −78° C. The mixture was warmed up to room temperature and stirred for 12 hours. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate till pH becomes 6-7 and extracted with ethyl acetate (50 mL×4). The combined organic layers were washed with water (60 mL×2) and saturated aqueous sodium chloride (60 mL×2) in turn, 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)=1/20, 500 mL) to give the title compound 25e as a white solid (1.28 g, 54.5%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 545.3[M+HCOO]−.

Provenance & Evidence