反应 #1178481

ord-5d08c030dd9e4d2787fb6e9517c13714

反应方程式

Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate
Cc1ccc(S(=O)(=O)OC[C@@H](O)[C@H](O)COS(=O)(=O)c2ccc(C)cc2)cc1
title compound
Cc1ccc(S(=O)(=O)OC[C@@H](O)[C@H](O)COS(=O)(=O)c2ccc(C)cc2)cc1
1,4-Di-O-tosyl-D-threitol

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.ADDITIONwas added
  2. 2
    温度the mixture was heated
  3. 3
    温度to reflux for 4 days
  4. 4
    温度The reaction liquor was cooled
  5. 5
    浓缩the solvent was concentrated under reduced pressure
  6. 6
    workup.ADDITIONA saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added to the obtained residue
  7. 7
    萃取the mixture was extracted with ethyl acetate
  8. 8
    洗涤The extract was washed with saturated brine
  9. 9
    干燥dried over anhydrous sodium sulfate
  10. 10
    浓缩concentrated under reduced pressure

实验过程

To an ethanol (100 mL) suspension of 1,4 di-O-tosyl-2,3-O-isopropylidene-L-threitol (10.0 g, 21.25 mmol), p-toluenesulfonic acid monohydrate (0.40 g) was added, and the mixture was heated to reflux for 4 days with stirring. The reaction liquor was cooled, and then the solvent was concentrated under reduced pressure. A saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to obtain the title compound as a solid. This compound was used in the subsequent reaction without performing further purification.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08129366B2uspto-grants-2012_03