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[ CAS No. 209746-56-5 ] {[proInfo.proName]}

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Chemical Structure| 209746-56-5
Chemical Structure| 209746-56-5
Structure of 209746-56-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 209746-56-5 ]

CAS No. :209746-56-5 MDL No. :N/A
Formula : C24H26O9 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 458.46 Pubchem ID :-
Synonyms :

Safety of [ 209746-56-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 209746-56-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 209746-56-5 ]

[ 209746-56-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1634-34-0 ]
  • [ 209746-56-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 81 percent / benzyltributylammonium chloride; aq. K2CO3 / CHCl3 / 27 h / 20 °C 2.1: 50 percent aq. KOH / ethanol / 0.17 h / 20 °C 2.2: ethanol / 16 h / 20 °C 3.1: 4-(dimethylamino)pyridine / 10 percent Pt/C / ethanol; H2O / 9 h / 20 °C
  • 2
  • [ 110-85-0 ]
  • aqueous potassium hydroxide [ No CAS ]
  • [ 10035-16-2 ]
  • [ 209746-55-4 ]
  • [ 209746-56-5 ]
YieldReaction ConditionsOperation in experiment
palladium-carbon; In ethanol; N,N-dimethyl acetamide; Example 21 2'-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxy-4'-methylacetophenone (100 g) is dissolved in a mixture of chilled ethanol (800 ml) and 50% aqueous potassium hydroxide solution (200 g), and thereto is added 5-formylbenzo[b]furan (30.91 g). The mixture is stirred at room temperature overnight under argon atmosphere. To the reaction mixture are added N,N-dimethylacetamide (400 ml), anhydrous piperazine (17.35 g) and 10% palladium-carbon (51.4% aqueous, 9.4 g), and the mixture is stirred at room temperature for two hours under atmospheric pressure of hydrogen gas. The catalyst is removed by filtration, and the filtrate is washed with diisopropyl ether, and acidified with 18% hydrochloric acid under ice-cooling. The mixture is extracted with ethyl acetate, and 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 crystallized twice from water-acetonitrile to give colorless crystals (66.86 g), which is combined with the compound (137.6 g) prepared by the same procedure. The combined product (204.46 g) is recrystallized from water-ethanol to give 3-(5-benzo[b]furanyl)-2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (195.70 g). The physicochemical properties of the compound are the same as those of the compound obtained in Example 1.
  • 3
  • aqueous potassium hydroxide [ No CAS ]
  • platinum carbon [ No CAS ]
  • [ 10035-16-2 ]
  • [ 209746-55-4 ]
  • [ 209746-56-5 ]
YieldReaction ConditionsOperation in experiment
With dmap; In ethanol; Example 1 2'-(2,3,4,6-Tetra-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxy-4'-methylacetophenone (120 g) is dissolved in a chilled mixture of ethanol (1.2 l) and 50% aqueous potassium hydroxide solution (240 g), and thereto is added 5-formylbenzo[b]furan (42.4 g), and the mixture is stirred at room temperature overnight under argon atmosphere. To the reaction solution are added 4-dimethylaminopyridine (29.5 g) and 10% platinum-carbon (23.58 g), and the mixture is stirred at room temperature for 4.5 hours under atmospheric pressure of hydrogen gas. The catalyst is removed by filtration, and the filtrate is washed with toluene, and acidified with 18% hydrochloric acid under ice-cooling. The mixture is extracted with ethyl acetate, and the organic layer is washed successively with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution. The washed aqueous layer is extracted with ethyl acetate, and the organic layers are combined, dried, and concentrated under reduced pressure. The residue is crystallized from water-ethanol to give 3-(5-benzo[b]furanyl)-2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (82.4 g). m.p. 152.5-154 C. ESI-MS (m/z): 476 [(M+NH4)+ ] IR (nujol, cm-1): 3560, 3510, 3350, 3270, 1630 NMR (DMSO-d6) delta: 2.24 (3H, s), 3.00 (2H, t, J=7.4, the unit of 1, coupling constant, is Hz, hereinafter, the same), 3.1-3.5 (7H, m), 3.71(1H, ddd, f=2.0, 5.5, 12), 4.59 (1H, t, J=5.8), 4.98 (1H, d, J=7.3), 5.05 (1H, d, J=5.1), 5.12 (1H, d, J=4.6), 5.29 (1H, d, J=5.1), 6.40 (1H, d, J=0.4), 6.54 (1H, s), 6.88 (1H, dd, J=0.9, 2.2), 7.22 (1H, dd, J=1.8, 8.4), 7.46 (1H, d, J=8.6), 7.53 (1H, d, J=1.5), 7.93 (1H, d, J=2.2), 11.90 (1H, s)
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