Sodium Methoxide → HCID 22872063, compound

HRID 54199Notes

Reaction equation

HRID 54199 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@H:8]([CH3:19])[O:7][C@H:6]1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31])(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=2)[C:30]([O:32][CH3:33])=[O:31])[O:7][C@@H:8]([CH3:19])[C@@H:9]([OH:15])[C@@H:10]([OH:11])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86750720Methyl 3-(2-(2,3,4-tri-O acetyl-alpha-L-fucopyranosyloxy)phenyl)benzoate

Product 1

HCID 22872063HCID 22872063, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was flushed through silica gel with 7:3 methylene chloride/methanol which

Sources & evidence

ORD record
ord-c743335eacde4eb380403503986ba8ee
Source dataset
uspto-grants-1997_04
Patent number
US05622937

Reaction notes

Loading…