HCID 10937019, compound → HCID 53736212, compound

HRID 901801Notes

Reaction equation

HRID 901801 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 subjected to celite filtration and the filtered product was washed with methanol. The filtrate 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 subjected to celite filtration
  2. washthe filtered product was washed with methanol
  3. distillationdistilled off under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-acecae11c01940ff98dfdff40e4dfeb2
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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