4-Toluenesulfonyl chloride → 1-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-alpha-D-glucose

HRID 2224016Notes

Reaction equation

HRID 2224016 reaction equation
[CH2:1]([O:4][C@H:5]1[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]([OH:9])[C@H:6]1[OH:7])[CH:2]=[CH2:3].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH2:1]([O:4][C@H:5]1[O:13][C@H:12]([CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[C@@H:10]([OH:11])[C@H:8]([OH:9])[C@H:6]1[OH:7])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10878666alpha-D-Glucopyranose, O-2-propenyl-

Product 1

HCID 866440821-O-(2-propenyl)-6-O-(4-tolylsulfonyl)-alpha-D-glucose

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Into 200 mL of anhydrous pyridine, 6.3 g (28.6 mmol) of the compound (IV) was dissolved, and 195 mg of p-dimethylaminopyridine (DMAP) and 7.0 g of p-toluenesulfonyl chloride were added. The solution was reacted for 16 hours at room temperature while stirring. Thereafter, the reaction was quenched by adding 20 mL of cold distilled water, and the reaction mixture was extracted with ethyl acetate (3×200 mL). The organic layers were combined, neutralized to pH 4 with 1.0 M and 0.1 M hydrochloric acids, washed with brine (2×200 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel flash chromatography (dichloromethane:methanol=20:1) (yield: 8.6 mg (23.0 mmol), recovery: 83.8%).

Workup

  1. customThe solution was reacted for 16 hours at room temperature
  2. customThereafter, the reaction was quenched
  3. additionby adding 20 mL
  4. distillationof cold distilled water
  5. extractionthe reaction mixture was extracted with ethyl acetate (3×200 mL)
  6. washwashed with brine (2×200 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by silica gel flash chromatography (dichloromethane:methanol=20:1) (yield: 8.6 mg (23.0 mmol), recovery: 83.8%)

Sources & evidence

ORD record
ord-c719860eaa8b4b80af78ce21b8b27144
Source dataset
uspto-grants-2008_05
Patent number
US07378398B2

Reaction notes

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