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Citric Acid → HCID 21967941, 화합물

HRID 1003941
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HRID 1003941 반응식
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2.N1C(C)=CC(C)=CC=1C.[P:46](Cl)([O:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([O:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:47].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][P:46]([O:48][C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)([O:55][C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)=[O:47])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 79532,4,6-TrimethylpyridineHCID 75654Diphenyl chlorophosphateHCID 10601391HCID 10601391, 화합물

생성물 1

HCID 21967941HCID 21967941, 화합물수율 74.4%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (300 mg) obtained in Example 2 is dissolved in tetrahydrofuran (3 ml), and thereto are added 2,4,6-collidine (315 mg) and diphenyl chlorophosphate (486 mg) under ice-cooling. The mixture is stirred at room temperature for 22 hours under argon atmosphere. The reaction mixture is poured into chilled 10% aqueous citric acid solution, and extracted with ethyl acetate. The organic layer is washed successively with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]furanyl)-2'-(6-O-diphenylphosphono-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (327 mg).

후처리

  1. temperaturecooling
  2. additionThe reaction mixture is poured
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed successively with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

출처 및 근거

ORD 기록
ord-463a7b61bf344a2b95d9db2ea7ae663c
출처 데이터셋
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06048842

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