Water → 1,6-Anhydro-4-O-benzyl-3-deoxy-2-O-p-toluenesulphonyl-beta-D-arabino-hexopyranose

HRID 728207ノート

反応式

HRID 728207 の反応式
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@@H:11]([OH:17])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O.C(Cl)(Cl)Cl>N1C=CC=CC=1>[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@@H:11]([O:17][S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 67930821HCID 67930821、化合物

生成物 1

HCID 867450351,6-Anhydro-4-O-benzyl-3-deoxy-2-O-p-toluenesulphonyl-beta-D-arabino-hexopyranose収率 85.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 1,6-anhydro-4-O-benzyl-3-deoxy-β-D-arabinohexopyranose (see Example 2) (2.0 g) in dry pyridine (30 ml) containing p-toluenesulphonyl chloride (2.0 g) was allowed to stand at room temperature for 24 h. Water (0.5 ml) was added and five minutes later chloroform (100 ml). The mixture was washed with water (×2), 2M aqueous hydrochloric acid, 1M aqueous sodium hydroxide, and water. The organic layer was dried (MgSO4) and concentrated to a light yellow syrup. Trituration with ethanol gave crystalline title compound (2.83 g, 83%).

後処理

  1. washThe mixture was washed with water (×2), 2M aqueous hydrochloric acid, 1M aqueous sodium hydroxide, and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated to a light yellow syrup

出典と根拠

ORDレコード
ord-6cb37d9a9c5544b88712e24f469ac9f2
出典データセット
uspto-grants-1991_09
特許番号
US05047518

反応ノート

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