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Nitromethane → 1-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)-3-nitropropan-2-one

HRID 2042930
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HRID 2042930 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47][C:48](O)=[O:49].C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:63]([CH3:66])([O-:65])=[O:64].[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47][C:48](=[O:49])[CH2:66][N+:63]([O-:65])=[O:64]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6375NitromethaneHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 67289388HCID 67289388, 화합물

생성물 1

HCID 866808891-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)-3-nitropropan-2-one수율 99.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a anhydrous THF (22 mL) solution of the carboxylic acid 55 (2.97 g, 4.28 mmol) was added 1,1′-carbonyl diimidazole (800 mg, 4.93 mmol) at room temperature. In separate flask, nitromethane (0.92 mL, 17.12 mmol) was added to a THF (9 mL) solution of NaH (200 mg, 4.93 mmol). The resulting white suspension was stirred at room temperature for 3 h. Then the prepared acyl imidazole solution was added to the suspension through a cannula at room temperature. After the transfer, the mixture was heated to 50° C. for 1.5 h. It was cooled to room temperature and quenched with 1.0 M HCl. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound (3.13 g, 99%).

후처리

  1. temperatureAfter the transfer, the mixture was heated to 50° C. for 1.5 h
  2. temperatureIt was cooled to room temperature
  3. customquenched with 1.0 M HCl
  4. extractionThe organic layer was extracted with ethyl acetate
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica column chromatography

출처 및 근거

ORD 기록
ord-23aed3c3f7b94636b8fbd67895b4048f
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08586550B2

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