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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1160175
[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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Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-876c049d97ad493d9d88665d6165e495
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07816328B2

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