Reaction Steps
(2S,3S,4R,5S,6R)-2-(3-(4-hydroxybenzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (37, 2.01 g, 4.0 mmol), ((3-bromopropoxy)methyl)benzene (1.41 mL, 8.0 mmol), Bu4NI (148 mg, 0.40 mmol), and K2CO3 (2.76 g, 20 mmol) were combined in DMF (8 mL) under nitrogen and stirred overnight at room temperature. The reaction was diluted with Et2O, washed with saturated aqueous NaHCO3 and brine (with back extraction), dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (gradient 0-50% EtOAc/hexanes) to give alkylated product 47 as a glassy solid (2.36 g, 91% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.28-7.36 (m, 5 H), 7.10-7.18 (m, 2 H), 7.03 (s, 1 H), 6.97 (d, J=8.6 Hz, 2 H), 6.77-6.84 (m, 2 H), 5.33 (t, J=9.6 Hz, 1 H), 5.21 (t, J=9.6 Hz, 1 H), 5.12 (t, J=9.6 Hz, 1 H), 4.48-4.54 (m, 3 H), 4.38 (d, J=9.9 Hz, 1 H), 4.06 (t, J=6.3 Hz, 2 H), 3.83-3.96 (m, 2H), 3.66 (t, J=6.2 Hz, 2 H), 2.21 (s, 3 H), 2.17 (s, 3 H), 2.10 (s, 3H) 2.04-2.12 (m, 2 H), 2.01 (s, 3 H), 1.75 (s, 3 H); MS (ES+) [M+NH4]+=668.
