HCID 118005630, compound → HCID 117996279, compound

HRID 1488273Notes

Reaction equation

HRID 1488273 reaction equation
C([O:4][C@H:5]1[C@H:14]([O:15]C(=O)C)[C@@H:13]([CH2:19][O:20]C(=O)C)[O:12][CH:7]([O:8][CH2:9][CH2:10][Cl:11])[C@@H:6]1[F:24])(=O)C.O(C)[Na]>CO>[F:24][C@@H:6]1[C@@H:5]([OH:4])[C@H:14]([OH:15])[C@@H:13]([CH2:19][OH:20])[O:12][CH:7]1[O:8][CH2:9][CH2:10][Cl:11]

Participants

4

Reactant 2

HCID 118005630HCID 118005630, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 117996279HCID 117996279, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloroethyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-glucopyranoside (0.85 g, 2.293 mmol) in CH3OH (10 mL) was added NaOCH3 (0.46 mL, 0.230 mmol, 0.5 M in CH3OH). The resulting mixture was stirred at rt for 2 hr. Dowex 50wx2-200 (H) ion exchange resin (pre-washed with CH3OH 3×10 mL) was added to the reaction mixture. After stirring for 15 min, the resin was filtered off and the filtrate was concentrated down to give the title compound. This anomeric mixture was used directly in the next step without further purification. TLC: silica gel, hexane/EtOAc: 1/1, Rf=0.2.

Workup

  1. washDowex 50wx2-200 (H) ion exchange resin (pre-washed with CH3OH 3×10 mL)
  2. additionwas added to the reaction mixture
  3. stirringAfter stirring for 15 min
  4. filtrationthe resin was filtered off
  5. concentrationthe filtrate was concentrated down

Sources & evidence

ORD record
ord-9644514b33744491a7f4dd9c4c73462e
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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