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 1160175Notes

Reaction equation

HRID 1160175 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-876c049d97ad493d9d88665d6165e495
Source dataset
uspto-grants-2010_10
Patent number
US07816328B2

Reaction notes

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