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

HRID 2224016노트

반응식

HRID 2224016 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-c719860eaa8b4b80af78ce21b8b27144
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378398B2

반응 노트

불러오는 중…