Sodium Methoxide → HCID 22872063, compound

Participants

Reaction Steps

Part E: Methyl 3-(2-(2,3,4-tri-O acetyl-α-L-fucopyranosyloxy)phenyl)benzoate (1.08 g, 1.45 mmol) was dissolved in methanol (25 ml) in a 50 ml flask, then treated with sodium methoxide (100 mg) and the mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was flushed through silica gel with 7:3 methylene chloride/methanol which provided methyl 3-(2-(α-L-fucopyranosyloxy)phenyl)benzoate (0.48 g, 59%) as a white solid, m.p.: 137°-140° C.; 1H NMR (300 MHz, CDCl3): 8.27 (s, 1H), 8.00 (d, J=8, 1H), 7.75 (d, J=8, 1H), 7.51 (t, J=8, 1H), 7.32-7.44 (comp, 3H), 7.10-7.20 (comp, 1H), 5.54 (d, J=2.7, 1H), 3.94 (s, 3H), 3.60-4.10 (comp, 7H), 1.26 (d, J=6, 3H); IR (KBr): 3421, 2938, 1718, 1437, 1245, 1083, 1035, 964, 844, 763; analysis: calculated for C20H22O7.0.25[H2O]: 63.4% C; 6.0% H. found: 63.3% C; 5.9% H.

Provenance & Evidence