Lithium Hydroxide → HCID 70873250, compound

Participants

Reaction Steps

Step-XI: To a stirred solution of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-2-methylsulfanyl-tetrahydro-pyran-3-yl ester (80 mg, 0.14 mmol) in methanol:THF:water (3:2:1 mixture, 6 ml) was added lithium hydroxide (9 mg, 0.4 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 55 mg of (2S,3R,4R,5S)-2-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-6-methylsulfanyl-tetrahydro-pyran-3,4,5-triol. 1H NMR (400 MHz, CD3OD): δ 0.52-0.60 (m, 2H), 0.80-0.90 (m, 2H), 1.78-1.88 (m, 1H), 2.15 (s, 3H), 3.32-3.35 (m, 3H), 4.05 (q, J=15.2 Hz, 2H), 4.11 (d, J=8.8 Hz, 1H), 4.17 (s, 4H), 4.38 (d, J=10 Hz, 1H), 6.61 (d, J=8.0 Hz, 2H), 6.69 (d, J=8.4 Hz, 1H), 6.98 (d, J=8.0 Hz, 1H), 7.15 (d, J=7.6 Hz, 1H), 7.17 (d, J=8.0 Hz, 1H). MS (ES) m/z 462.3 (M+18).

Provenance & Evidence