Hydrochloric Acid → 2'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

HRID 230891

Reaktionsgleichung

Reaktionsgleichung von HRID 230891
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH3:18][C:19]([O:21][CH2:22][C@H:23]1[O:28][C@H:27](Br)[C@H:26]([O:30][C:31]([CH3:33])=[O:32])[C@@H:25]([O:34][C:35]([CH3:37])=[O:36])[C@@H:24]1[O:38][C:39]([CH3:41])=[O:40])=[O:20].Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)(Cl)Cl.O>[C:31]([O:30][C@@H:26]1[C@@H:25]([O:34][C:35](=[O:36])[CH3:37])[C@H:24]([O:38][C:39](=[O:40])[CH3:41])[C@@H:23]([CH2:22][O:21][C:19](=[O:20])[CH3:18])[O:28][C@H:27]1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10])(=[O:32])[CH3:33]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 696872',6'-DihydroxyacetophenoneHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

Produkt 1

HCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenoneAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 159952Benzyltributylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a mixture of 2′,6′-dihydroxyacetophenone (1 g), potassium carbonate (4.54 g) and benzyltri(n-butyl)ammonium chloride (0.41 g) in chloroform (13 mL) were added water (0.5 mL) and acetobromo-α-D-glucose (2.7 g), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and the mixture was acidified by addition of 2 mol/L hydrochloric acid. The resulting mixture was extracted with ethyl acetate, and the extract was washed with water and brine. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was treated with methanol, and the precipitated crystals were collected by filtration and dried under reduced pressure to give the title compound (1.38 g).

Aufarbeitung

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and brine
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. additionThe residue was treated with methanol
  6. filtrationthe precipitated crystals were collected by filtration
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9d240b3dce7d47339874ef7064ae6587
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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