Benzyl Bromide → α-D-Glucopyranuronic acid, 1-deoxy-1-fluoro-, phenylmethyl ester

HRID 397233Notes

Reaction equation

HRID 397233 reaction equation
[F:1][C@H:2]1[O:10][C@H:9]([C:11]([O-:13])=[O:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[F:1][C@H:2]1[O:10][C@H:9]([C:11]([O:13][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 23681734HCID 23681734, compound

Product 1

HCID 15735492α-D-Glucopyranuronic acid, 1-deoxy-1-fluoro-, phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium 1-deoxy-1-fluoro-α-D-glucuronate (6.22 g, 28.51 mmol) was suspended in DMF (350 ml), and benzyl bromide (4.89 g, 28.59 mmol) was added. The reaction mixture was stirred at 60° C. for 24 h and then evaporated. The residue was dissolved in 3:1 chloroform/methanol, and magnesium sulfate (12 g) was added. The suspension was stirred for 2 h and then filtered, and the filtrate was evaporated. The residue was purified by column chromatography on silica gel (160 g) with 4:1 dichloromethane/acetone.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in 3:1 chloroform/methanol, and magnesium sulfate (12 g)
  3. additionwas added
  4. stirringThe suspension was stirred for 2 h
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customThe residue was purified by column chromatography on silica gel (160 g) with 4:1 dichloromethane/acetone

Sources & evidence

ORD record
ord-3ce60e46f5aa4f5dafddfcc88ee5a1aa
Source dataset
uspto-grants-2003_08
Patent number
US06610299B1

Reaction notes

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