Lithium Hydroxide → HCID 66562317, compound

Participants

Reaction Steps

Step-IV: To a stirred solution of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-2-methoxy-tetrahydro-pyran-3-yl ester (300 mg, 0.55 mmol) in methanol:THF:water (3:2:1 mixture, 6 ml) was added lithium hydroxide (46 mg, 1.10 mmol). After stirring for 2 h at room temperature, volatiles were evaporated under reduced pressure. The resulting residue was taken in ethyl acetate (10 ml) and washed with brine (5 ml), brine containing 1 ml of 5% aqueous KHSO4 (5 ml), brine (5 ml), dried over sodium sulfate, concentrated and purified by preparative HPLC to furnish 90 mg (2S,3R,4R,5S,6S)-2-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol as white solid. 1H NMR (400 MHz, CD3OD): δ 0.56-0.58 (m, 2H), 0.84-0.87 (m, 2H), 1.80-1.85 (m, 1H), 3.27-3.44 (m, 3H), 3.48 (s, 3H), 4.05 (d, J=6.4 Hz, 2H), 4.10 (d, J=9.3 Hz, 1H), 4.17 (s, 4H), 4.30 (d, J=7.8 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 6.69 (d, J=8.4 Hz, 2H), 6.98 (d, J=7.8 Hz, 1H), 7.16-7.19 (m, 2H). MS (ES) m/z 446.3 (M+18).

Provenance & Evidence