Dibutyltin oxide → p-Nitrophenyl 3-O-methyl-beta-L-fucopyranoside

HRID 1274105Notes

Reaction equation

HRID 1274105 reaction equation
[O:1]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[C@H:2]1[O:10][C@@H:9]([CH3:11])[C@@H:7]([OH:8])[C@@H:5]([OH:6])[C@@H:3]1[OH:4].[CH2:21]([Sn](=O)CCCC)CCC>CO>[CH3:21][O:6][C@@H:5]1[C@H:7]([OH:8])[C@H:9]([CH3:11])[O:10][C@H:2]([O:1][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[C@H:3]1[OH:4]

Participants

4

Reactant 2

HCID 61221Dibutyltin oxideHCID 896094-Nitrophenyl 6-deoxy-beta-L-galactopyranoside

Product 1

HCID 18336706p-Nitrophenyl 3-O-methyl-beta-L-fucopyranosideYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

6 g (21 mmol) of p-nitrophenyl β-L-fucopyranoside in 300 ml of absol. methanol are treated with 7.84 g (31.5 mmol) of dibutyl tin oxide and heated under reflux for 2 h. The mixture is then concentrated, and the residue is dried and then taken up in 300 ml of DMF. After addition of 15.7 ml of methyl iodide, the batch is stirred at 70° C. for 40 h. The solvent is removed under reduced pressure and the residue is taken up in 300 ml of dichloromethane. The suspension is filtered, and the solution that remains is concentrated again and subjected to flash chromatography (dichloromethane/methanol 99:1). The concentration gives 3.82 g (61%) of the target product.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture is then concentrated
  4. customthe residue is dried
  5. additionAfter addition of 15.7 ml of methyl iodide
  6. customThe solvent is removed under reduced pressure
  7. filtrationThe suspension is filtered
  8. concentrationthe solution that remains is concentrated again
  9. concentrationThe concentration

Sources & evidence

ORD record
ord-b77b79a0c28f4421bbf7b7fd51d82fb9
Source dataset
uspto-grants-2000_12
Patent number
US06156754

Reaction notes

Loading…