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

HRID 728207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728207
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 867450351,6-Anhydro-4-O-benzyl-3-deoxy-2-O-p-toluenesulphonyl-beta-D-arabino-hexopyranoseAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6cb37d9a9c5544b88712e24f469ac9f2
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047518

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