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Sodium Hydroxide → (2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-1H-indol-5-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

HRID 1160175
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HRID 1160175 반응식
[CH2:1]([C:3]1[CH:57]=[CH:56][C:6]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C@@H:17]4[O:46][C@H:45]([CH2:47][O:48]CC5C=CC=CC=5)[C@@H:36]([O:37]CC5C=CC=CC=5)[C@H:27]([O:28]CC5C=CC=CC=5)[C@H:18]4[O:19]CC4C=CC=CC=4)[CH:15]=3)[NH:10][CH:9]=2)=[CH:5][CH:4]=1)[CH3:2].[OH-].[Na+]>C1COCC1.O>[CH2:1]([C:3]1[CH:57]=[CH:56][C:6]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C@@H:17]4[O:46][C@H:45]([CH2:47][OH:48])[C@@H:36]([OH:37])[C@H:27]([OH:28])[C@H:18]4[OH:19])[CH:15]=3)[NH:10][CH:9]=2)=[CH:5][CH:4]=1)[CH3:2]
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 686322493-(4-Ethylbenzyl)-5-(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)-1H-indole

생성물 1

HCID 11234901(2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-1H-indol-5-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 8028
Tetrahydrofuran
용매

실험 절차

3-(4-Ethylbenzyl)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1H-indole: Part E (0.68 g, 0.78 mmol) was dissolved in THF (15 mL) and 25% aqueous sodium hydroxide (5 mL) and the resulting solution was brought to reflux for 3 h. After cooling to room temperature, the mixture was diluted with water (30 mL), and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by chromatography on silica gel eluting with ethyl acetate/hexane (1:3) to provide the title compound (0.5 g, 85%) as white solid.

후처리

  1. temperatureto reflux for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica gel eluting with ethyl acetate/hexane (1:3)

출처 및 근거

ORD 기록
ord-876c049d97ad493d9d88665d6165e495
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816328B2

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