HCID 10937019, compound → HCID 53736212, compound

HRID 549472Notes

Reaction equation

HRID 549472 reaction equation
[C:1]([O:4][C@@H:5]1[O:18][C@H:17]([CH2:19][O:20]C(=O)C)[C@@H:12]([O:13]C(=O)C)[C@H:7]([O:8]C(=O)C)[C@H:6]1[F:24])(=O)C>CO>[F:24][C@@H:6]1[C@@H:7]([OH:8])[C@H:12]([OH:13])[C@@H:17]([CH2:19][OH:20])[O:18][CH:5]1[O:4][CH3:1]

Participants

3

Reactant 1

HCID 10937019HCID 10937019, compound

Product 1

HCID 53736212HCID 53736212, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

1,3,4,6-tetra-O-Acetyl-2-deoxy-2-fluoro-β-D-glucopyranose (Carbohydr. Res., 153, 1986, 168-170) (13.4 g, 38.3 mmol) was dissolved in methanol (150 mL) and Dowex 50w×8 (19 g) was added thereto, followed by stirring of the mixture at 80° C. for 12 hours. The reaction mixture was filtered through Celite and the filtered product was washed with methanol. The filtered product and the washing liquid were combined and distilled off under reduced pressure. The residue was purified using silica gel flash column chromatography (methylene chloride:methanol, 10:1-5:1, V/V) to obtain the desired title compound (3.37 g, yield: 45%) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filtered product was washed with methanol
  3. distillationdistilled off under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-494d7d819c604b2b8daf794ff6b4419a
Source dataset
uspto-grants-2011_05
Patent number
US07943584B2

Reaction notes

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