O-acetylglucal → 4,6-di-O-acetylglucal

HRID 1422548Notes

Reaction equation

HRID 1422548 reaction equation
C([O:4][C@H:5]1[C@H:10]([OH:11])[C@@H:9]([CH2:12][OH:13])[O:8][CH:7]=[CH:6]1)(=O)C>[PH5].[Cl-].[Na+].O>[C:5]([O:11][C@@H:10]1[C@@H:9]([CH2:12][O:13][C:9](=[O:8])[CH3:10])[O:8][CH:7]=[CH:6][C@H:5]1[OH:4])(=[O:4])[CH3:6]

Participants

4

Reactant 1

HCID 14376821O-acetylglucal

Product 1

HCID 143081174,6-di-O-acetylglucalYield 189.1%

Reagents, catalysts & solvents 2

HCID 57417360Sodium chloride; waterSolventHCID 178527699HCID 178527699, compoundSolvent

Procedure

Per-O-acetyl glucal (27.5 mmol) was dissolved in phosphorane buffer (80 mL). Amano lipase (4.0 g) was added and the reaction mixture was stirred at room temperature for 24 hr. Brine (200 mL) was added and the obtained mixture was extracted with ethyl acetate (3×150 mL). Combined organic extracts were filtered trough Celite, and dried over anhydrous sodium sulfate. Drying agent and solvent were removed and product was purified by column chromatography (SilicaGel 60) using hexanes:ethyl acetate as eluents. 4,6-Di-O-Acetyl-D-glucal (26 mmol, yield 96%) was obtained.

Workup

  1. additionAmano lipase (4.0 g) was added
  2. extractionthe obtained mixture was extracted with ethyl acetate (3×150 mL)
  3. filtrationCombined organic extracts were filtered trough Celite
  4. dry with materialdried over anhydrous sodium sulfate
  5. customDrying agent and solvent
  6. customwere removed
  7. customproduct was purified by column chromatography (SilicaGel 60)

Sources & evidence

ORD record
ord-4d99e80bdf1144f3baf55826f3ca5e1b
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

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