Sodium Methoxide → HCID 53958828, compound

Participants

Reaction Steps

To a solution of crude phenyl 6-deoxy-3,4-di-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-allopyranoside β-13 in 20 mL of MeOH is added NaOMe (200 mg, 3.8 mmol). The reaction mixture is stirred at room temperature for 2 h and then neutralized with Amberlite resin. The solution is filtered, washed several times with MeOH and concentrated in vacua. The crude product is purified by flash chromatography (60% EtOAc/petroleum ether) to afford 1.01 g (72%, 3 steps) of phenyl 6-deoxy-2-O-(4-methoxybenzyl)-1-thio-β-L-allopyranoside (β-14): Rf 0.35 (50% EtOAc/petroleum ether); 1H NMR (CDCl3, 270 MHz) δ 7.56-7.52 (m, 2H, ArH), 7.31-7.27 (m, 5H, ArH), 6.89-6.88 (m, 2H, ArH), 4.93 (d, J=9.9 Hz, 1H, H-1), 4.71 (d, J=11.2 Hz, 1H, CH2), 4.55 (d, J=11.2 Hz, 1H, CH2), 4.13 (t, J=2.6 Hz, 1H, H-3), 3.83 (s, 3H, OCH3), 3.73-3.63 (m, 1H, H-5), 3.38 (dd, J=3.3, 9.9 Hz, 1H, H-2), 3.21 (dt, J=3.3, 9.6 Hz, 1H, H-4), 2.58 (s, 1H, OH) 2.34-2.30 (d, 1H, OH), 1.33 (d, J=6.3 Hz, 3H, H-6).

Provenance & Evidence