Water → HCID 86745035, compound

HRID 728207Notes

Reaction equation

HRID 728207 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 86745035HCID 86745035, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6cb37d9a9c5544b88712e24f469ac9f2
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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