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

HRID 230891

反応式

HRID 230891 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone収率 43.6%

試薬・触媒・溶媒 3

HCID 159952Benzyltributylammonium chloride触媒HCID 962Water溶媒2 回HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9d240b3dce7d47339874ef7064ae6587
出典データセット
uspto-grants-2009_07
特許番号
US07566699B2

関連ノート

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