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

HRID 728207노트

반응식

HRID 728207 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 67930821HCID 67930821, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6cb37d9a9c5544b88712e24f469ac9f2
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05047518

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