Lithium Hydroxide → HCID 76071002, compound

Participants

Reaction Steps

(2S,3S,4R,5S,6R)-2-(3-(4-(4-methoxy-4-oxobutyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (9, 1.65 g, 2.81 mmol) was dissolved in a MeOH/THF/H2O solution (25 mL, 2:1:2 vol. ratio). Lithium hydroxide (674 mg, 28.1 mmol) was added and the reaction stirred at room temperature for 1 hour. The reaction was acidified to pH=1-2 with saturated aqueous NaHSO4. The acidic aqueous layer was extracted three times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was rotovapped down once from hexanes to provide the product as white transferable solid (1.27 g, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.99 (s, 1 H), 6.96-7.16 (m, 7H), 5.16 (d, J=5.8 Hz, 1 H), 5.06 (d, J=4.3 Hz, 1 H), 4.82 (d, J=5.6 Hz, 1 H), 4.32 (d, J=9.6 Hz, 1H), 4.04 (d, J=9.1 Hz, 1 H), 3.90 (s, 2 H), 2.53 (t, J=7.3 Hz, 2 H), 2.19 (t, J=7.3 Hz, 2 H), 2.17 (s, 3H), 2.03 (s, 3 H), 1.76 (quin, J=7.6 Hz, 2 H). MS (ES+) [M+NH4]+=464.

Provenance & Evidence