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Chemical Structure| 1486-48-2 Chemical Structure| 1486-48-2

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Chemical Structure| 1486-48-2

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Product Details of [ 1486-48-2 ]

CAS No. :1486-48-2
Formula : C28H24O5
M.W : 440.49
SMILES Code : O=C(O)C1=CC(OCC2=CC=CC=C2)=C(OCC3=CC=CC=C3)C(OCC4=CC=CC=C4)=C1
MDL No. :MFCD00825832
InChI Key :NRCGMEJBEDWPMG-UHFFFAOYSA-N
Pubchem ID :11133969

Safety of [ 1486-48-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 1486-48-2 ]

* 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 [ 1486-48-2 ]

[ 1486-48-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 70424-94-1 ]
  • [ 1486-48-2 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide; In methanol; for 4h;Reflux; General procedure: Gallic acid (1.5 g,8.83 mmol) was dissolved in 9 cm3 methanol, conc.0.45 cm3 sulfuric acid was added thereto, and the mixturewas stirred under reflux for 5 h. The reaction vessel wascooled down to room temperature and the reaction mixturewas neutralized with saturated sodium bicarbonate solutionat 0 C. Then, the organic solvent was removed at reducedpressure, and the residue dissolved in ethyl acetate, washedwith saturated sodium bicarbonate solution, dried overanhydrous sodium sulfate, and concentrated to give methyl1.39 g 3,4,5-trihydroxybenzoate (7.55 mmol, 86% yield)as white solid. This compound was used in the next stepreaction without further purification.Gallic acid (1.5 g,8.83 mmol) was dissolved in 9 cm3 methanol, conc.0.45 cm3 sulfuric acid was added thereto, and the mixturewas stirred under reflux for 5 h. The reaction vessel wascooled down to room temperature and the reaction mixturewas neutralized with saturated sodium bicarbonate solutionat 0 C. Then, the organic solvent was removed at reducedpressure, and the residue dissolved in ethyl acetate, washedwith saturated sodium bicarbonate solution, dried overanhydrous sodium sulfate, and concentrated to give methyl1.39 g 3,4,5-trihydroxybenzoate (7.55 mmol, 86% yield)as white solid. This compound was used in the next stepreaction without further purification.A mixture of methyl 2.114 g 3,4,5-tris(benzyloxy)benzoate(4.66 mmol), sodium hydroxide (96 mmol), 6 cm3MeOH, and 12 cm3 dioxane was heated at reflux for 4 h.The solvent was removed and the resulting residue waspartitioned between water and ethyl acetate. The combinedorganic layers were washed with brine, dried (Na2SO4),and concentrated at reduced pressure to give the titlecompound (1.984 g, 4.51 mmol, 97% yield) as a whitesolid. Spectral data were in accordance with those previouslyreported
86% With potassium hydroxide; isopropyl alcohol; for 1h;Heating / reflux; To a mixture of methyl 3,4,5- tribenzyloxybenzoate (15) (20.60 g, 45.30 mmol) in 2-propanol (200 mL) was added a solution of potassium hydroxide (3.50 g, 85%, 53.00 mmol) in 2-propanol (25 mL). The mixture was refluxed for 1 h, cooled, and water was added (250 niL). A white precipitate appeared, and the mixture was filtered. Recrystallisation from ethyl acetate afforded the desired compound as white crystals, m.p. 194-195 0C Yield: 17.2 g (86%). 1H NMR (300 MHz, OMSO-d6): delta = 5.05 (2H, s), 5.18 (4H, s), 7.24-7.50 (17H, m), 13.4 (IH, s, broad); 13C NMR (75 MHz): delta = 70.3, 74.3, 108.3, 126.1, 127.7, 128.0, 128.2, 128.3, 128.5 , 136.9, 137.5, 141.0, 152.1, 167.0.
75% With water; sodium hydroxide; In 1,4-dioxane; methanol; at 120℃; for 6h;Inert atmosphere; To the stirred solution of compound 13 (1.93 g, 4.25 mmol) in MeOH (5 mL): dioxane (10 mL): H2O(4 mL), NaOH (0.8 g, 4.25 mmol) was added. The reaction mixture was heated under reflux for 6 h at 120 C, and evaporated. The residual mass was taken in water (20 mL) and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuum to afford compound 14 as white solid (1.77 g, 75%); mp = 274- 276 C, 1HNMR (CDCl3, 400 MHz); delta 5.12 (s, 6H), 7.26 (s, 2H), 7.37- 7.45 (m,15H); 13C NMR (CDCl3, 100 MHz) delta 71.2, 73.2, 109.5, 127.6(s), 127.9, 128 (s), 128.2 (s), 128.5 (s),136.5, 140.4, 152.6, 169.8; HRMS (ESI) m/z [C28H24NaO5] calcd for 463.1521 found 463.1536.
3.30 g With sodium hydroxide; In tetrahydrofuran; methanol; water; at 80℃; for 1h; To a solution of 8c (60.0 g, 0.318 mol) in MeOH (638 mL) was added SOCl2 (23.2 mL, 0.319 mol) fordropwise at 60 C. The reaction mixture was stirred at 60 C for 8 h. Then, the reaction mixture wasevaporated under reduced pressure. The crude mixture was applied to following reaction without furtherpurification.To a mixture of crude material (2.00 g, 10.9 mmol) and K2CO3 (6.78 g, 49.0 mmol) in DMF (36.0 mL)were added benzyl bromide (4.10 mL, 35.9 mmol) and TBAI (1.60 g, 4.33 mmol) at room temperature.The reaction mixture was stirred at room temperature for 11 h. Then, the reaction mixture was filteredthrough a pad of Celite, diluted with H2O, and extracted with CH2Cl2. The organic layer was washed withwater and brine, dried over anhydrous MgSO4, and evaporated under reduced pressure. The crude mixturewas applied to following reaction without further purification.To a stirred solution of crude residue in MeOH/THF (1/1, 36.3 mL) was added 4 M NaOH aq. (9.50 mL,38.0 mmol) at 80 C. The reaction mixture was stirred at 80 C for 1 h. Then, the reaction mixture wasquenched with 6 M HCl aq., and filtered. The filtrate was washed with H2O to give 9c (3.30 g, 7.49 mmol,68%) as a white solid.Spectral data for 9c were in good agreement with those reported in reference.16

References: [1]Monatshefte fur Chemie,2018,vol. 149,p. 1293 - 1300.
[2]Zeitschrift fur Naturforschung, B: Chemical Sciences,2009,vol. 64,p. 464 - 466.
[3]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1567 - 1570.
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 1609 - 1621.
[5]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2590 - 2593.
[6]New Journal of Chemistry,2011,vol. 35,p. 1541 - 1548.
[7]Phytochemistry,1999,vol. 52,p. 759 - 767.
[8]Patent: WO2006/134352,2006,A1 .Location in patent: Page/Page column 18;26-27.
[9]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 2051 - 2054.
[10]Chemistry - A European Journal,2012,vol. 18,p. 9063 - 9074.
[11]Tetrahedron Letters,2002,vol. 43,p. 8185 - 8189.
[12]Synthetic Communications,2006,vol. 36,p. 587 - 597.
[13]Tetrahedron Letters,2016,vol. 57,p. 2652 - 2654.
[14]Journal of the American Chemical Society,2013,vol. 135,p. 15609 - 15616.
[15]Journal of the American Chemical Society,1943,vol. 65,p. 85.
[16]Helvetica Chimica Acta,1962,vol. 45,p. 270 - 276.
[17]Chemical and Pharmaceutical Bulletin,2003,vol. 51,p. 1085 - 1088.
[18]Journal of Medicinal Chemistry,2006,vol. 49,p. 2829 - 2837.
[19]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7975 - 7982.
[20]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 190 - 194.
[21]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2191 - 2194.
[22]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 11081 - 11089.
[23]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 631 - 636,6.
[24]Tetrahedron Letters,2014,vol. 55,p. 275 - 278.
[25]Journal of Medicinal Chemistry,2014,vol. 57,p. 3724 - 3736.
[26]Heterocycles,2014,vol. 8,p. 1371 - 1396.
[27]European Journal of Medicinal Chemistry,2019,vol. 163,p. 560 - 568.
  • 2
  • [ 61439-59-6 ]
  • [ 1486-48-2 ]
  • 3,4,5-tris-benzyloxy-benzoic acid 2-(4-benzyloxy-phenyl)-ethyl ester [ No CAS ]
  • 3
  • [ 1486-48-2 ]
  • [ 863-03-6 ]
  • 4
  • [ 1486-48-2 ]
  • [ 618-73-5 ]
  • 5
  • [ 24259-59-4 ]
  • [ 1486-48-2 ]
  • 1,2,3,4-tetra-O-galloyl-L-ribopyranose [ No CAS ]
 

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