Benzenesulfonyl chloride → (rac)-1-O-octadecyl-2-O-benzenesulfonyl-3-O-trityl-glycerol

HRID 638532노트

반응식

HRID 638532 반응식
[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:44]1([S:50](Cl)(=[O:52])=[O:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>N1C=CC=CC=1.ClCCl.C(Cl)(Cl)Cl>[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:22][S:50]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=[O:52])=[O:51])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

6

반응물 2

HCID 7369Benzenesulfonyl chloride2회HCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

생성물 1

HCID 92035207(rac)-1-O-octadecyl-2-O-benzenesulfonyl-3-O-trityl-glycerol수율 98.9%

시약·촉매·용매 3

HCID 1049Pyridine용매2회HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (rac)-1-O-octadecyl-3-O-trityl-glycerol (30.52 g) in a mixture of pyridine (41.08 g) and dichloromethane (250 ml) was dropwise added a solution of benzenesulfonyl chloride (18.36 g) in chloroform (50 ml) during a period of 10 minutes below 10° C. After stirring for 2 days at ambient temperature, the reaction mixture was refluxed for 8 hours. To the reaction mixture, were dropwise added pyridine (12.75 g) and benzenesulfonylchloride (5.7 g) successively. After stirring for 2 hours at room temperature, the reaction mixture was allowed to stand for 2 days. The reaction mixture was washed with water, 0.5N aqueous sulfuric acid, water, aqueous sodium bicarbonate and water, successively. The solution was dried over magnesium sulfate and evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (450 g, elution by benzene) to give 37.4 g of (rac)-1-O-octadecyl-2-O-benzenesulfonyl-3-O-trityl-glycerol as an oil.

후처리

  1. temperaturethe reaction mixture was refluxed for 8 hours
  2. stirringAfter stirring for 2 hours at room temperature
  3. waitto stand for 2 days
  4. washThe reaction mixture was washed with water, 0.5N aqueous sulfuric acid, water, aqueous sodium bicarbonate and water
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give a residue, which
  8. customwas purified by column chromatography on silica gel (450 g, elution by benzene)

출처 및 근거

ORD 기록
ord-90069915e3a74fe2a9e9edfccd97c963
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562179

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