Acetone → beta-D-Glucopyranoside, 4-nitrophenyl, 2,3,4,6-tetraacetate

HRID 325284

反応式

HRID 325284 の反応式
[CH3:1][C:2]([O:4][CH2:5][C@H:6]1[O:11][C@H:10](Br)[C@H:9]([O:13][C:14]([CH3:16])=[O:15])[C@@H:8]([O:17][C:18]([CH3:20])=[O:19])[C@@H:7]1[O:21][C:22]([CH3:24])=[O:23])=[O:3].[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([O-:34])=[CH:30][CH:29]=1)([O-:27])=[O:26].[Na+].CC(C)=O.[OH-].[Na+]>O>[C:14]([O:13][C@@H:9]1[C@@H:8]([O:17][C:18](=[O:19])[CH3:20])[C@H:7]([O:21][C:22](=[O:23])[CH3:24])[C@@H:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[O:11][C@H:10]1[O:34][C:31]1[CH:32]=[CH:33][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=1)(=[O:15])[CH3:16]

参加物

6

反応物 4

HCID 180AcetoneHCID 13214p-nitrophenol sodium saltHCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

生成物 1

HCID 2747768beta-D-Glucopyranoside, 4-nitrophenyl, 2,3,4,6-tetraacetate収率 24.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a mixture of 15 g of acetobromoglucose, 7.92 g of sodium 4-nitrophenolate and 50 ml of acetone was added 300 mg of sodium hydroxide in 15 ml of water. This mixture was stirred for 18 hours, poured into 400 ml of water and the precipitate was filtered off. The residue was dissolved in 200 ml of methylene chloride, washed with 100 ml of aqueous sodium bicarbonate solution, dried and passed through a pad of hydrous magnesium silicate. Evaporation of the solvent and crystallization yielded 4.26 g of 4-nitrophenyl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside as white crystals, mp 173°-175° C.

後処理

  1. filtrationthe precipitate was filtered off
  2. dissolutionThe residue was dissolved in 200 ml of methylene chloride
  3. washwashed with 100 ml of aqueous sodium bicarbonate solution
  4. customdried
  5. customEvaporation of the solvent and crystallization

出典と根拠

ORDレコード
ord-024b2d207f1744f7a59120acf5ee5188
出典データセット
uspto-grants-1984_04
特許番号
US04440758

関連ノート

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