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Chemical Structure| 234081-96-0

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Product Details of [ 234081-96-0 ]

CAS No. :234081-96-0
Formula : C14H26O4
M.W : 258.35
SMILES Code : O=C(O)CCCCCCCCC(OC(C)(C)C)=O
MDL No. :MFCD28505598
InChI Key :FRIYHISQFBWFCN-UHFFFAOYSA-N
Pubchem ID :53814457

Safety of [ 234081-96-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 234081-96-0 ]

* 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 [ 234081-96-0 ]

[ 234081-96-0 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 693-55-0 ]
  • [ 115-11-7 ]
  • [ 234081-96-0 ]
  • 4
  • [ 234081-96-0 ]
  • [ 229467-51-0 ]
  • [ 497266-24-7 ]
  • 5
  • [ 234081-96-0 ]
  • 9-[(S)-2-((S)-1,2-Bis-hexadecylcarbamoyl-ethylcarbamoyl)-1-carboxy-ethylcarbamoyl]-nonanoic acid [ No CAS ]
  • 7
  • [ 234081-96-0 ]
  • tert-butyl (R)-10-[(R)-4-benzyl-2-oxooxazolidin-3-yl]-9-hydroxy-10-oxodecanoate [ No CAS ]
  • 8
  • [ 234081-96-0 ]
  • tert-butyl (R)-10-[(R)-4-benzyl-2-oxooxazolidin-3-yl]-9-[(tert-butyldimethylsilyl)oxy]-10-oxodecanoate [ No CAS ]
  • 9
  • [ 234081-96-0 ]
  • tert-butyl (R)-9-[(tert-butyldimethylsilyl)oxy]-10-hydroxydecanoate [ No CAS ]
  • 10
  • [ 234081-96-0 ]
  • tert-butyl (R)-9-[(tert-butyldimethylsilyl)oxy]-10-oxodecanoate [ No CAS ]
  • 11
  • [ 234081-96-0 ]
  • C34H66O5Si2 [ No CAS ]
  • 12
  • [ 234081-96-0 ]
  • C30H58O5Si2 [ No CAS ]
  • 13
  • [ 234081-96-0 ]
  • tert-butyl (9R,10E,13R,15Z)-9-[(tert-butyldimethylsilyl)oxy]-13-[(4-methoxybenzyl)oxy]-12-oxooctadeca-10,15-dienoate [ No CAS ]
  • 14
  • [ 234081-96-0 ]
  • (9R,10E,13R,15Z)-9-[(tert-butyldimethylsilyl)oxy]-13-[(4-methoxybenzyl)oxy]-12-oxooctadeca-10,15-dienoic acid [ No CAS ]
  • 15
  • [ 234081-96-0 ]
  • (9R,10E,13R,15Z)-9-[(tert-butyldimethylsilyl)oxy]-13-hydroxy-12-oxooctadeca-10,15-dienoic acid [ No CAS ]
  • 16
  • [ 234081-96-0 ]
  • (10R,14R,E)-10-[(tert-butyldimethylsilyl)oxy]-14-[(Z)-pent-2-en-1-yl]oxacyclotetradec-11-ene-2,13-dione [ No CAS ]
  • 18
  • [ 234081-96-0 ]
  • [ 372504-89-7 ]
  • tert-butyl (R)-10-(4-benzyl-2-oxooxazolidin-3-yl)-10-oxodecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% To a stirred solution of 12 (386 mg, 1.49 mmol) in THF (3 mL) were successively added Et3N (0.21 mL, 1.5 mmol) and pivaloyl chloride (0.18 mL, 1.5 mmol) at ?78 °C, and the mixture was stirred for 30 min. To the mixture was added dropwise a solution of A [prepared from (R)-4-benzyl-oxazolidin-2-one (290 mg, 1.64 mmol) and n-BuLi (2.6 M in hexane, 0.63 mL, 1.6 mmol) in THF (3.3 mL) at ?78 °C] at ?78 °C, and the mixture was warmed to room temperature, stirred overnight, quenched with satd aq NH4Cl, and then extracted with Et2O. The extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 column chromatography (hexane/EtOAc = 8:1 to 3:1) to give 13 (497 mg, 80 percent) as a colorless oil. [alpha]24D ?32.8 (c 1.19, CHCl3); IR: numax 1785 (vs), 1728 (s), 1704 (s), 1251 (m), 1212 (m) 1155 (m); 1H NMR: delta 1.24?1.41 (8H, m), 1.44 (9H, s), 1.53?1.62 (2H, m), 1.64?1.75 (2H, m), 2.20 (2H, t, J = 7.6 Hz), 2.76 (1H, dd, J = 9.6, 13.2 Hz), 2.89 (1H, dt, J = 17.0, 7.6 Hz), 2.97 (1H, dt, J = 17.2, 7.6 Hz), 3.30 (1H, dd, J = 3.2, 13.2 Hz), 4.16 (1H, dd, J = 3.2, 8.4 Hz), 4.20 (1H, t, J = 8.4 Hz), 4.68 (1H, ddt, J = 8.4, 9.6, 3.2 Hz), 7.18?7.23 (2H, m), 7.25?7.37 (3H, m); 13C NMR: delta 24.2, 25.0, 28.1 (3C), 29.00, 29.02, 29.1, 29.2, 35.5, 35.6, 37.9, 55.1, 66.1, 79.9, 127.3, 128.9 (2C), 129.4 (2C), 135.3, 153.4, 173.26, 173.35; HRMS (FAB): m/z calcd for C24H35O5Na, 440.2413; found, 440,2414 ([M+Na]+).
YieldReaction ConditionsOperation in experiment
General procedure: DMAP (2.80 g, 23.0 mmol) was added to a mixture of pentadecanedioic acid (25.0 g, 92.0 mmol) in 2-Me-THF (250 mL). After stirring at rt for 10 min, tert-butanol (13.2 mL, 138 mmol) was added and stirring was continued at rt for 10 min. After the resulting suspension was heated at 60° C. for 10 min, it became a clear colorless solution. A solution of BOC-anhydride (26.0 g, 119 mmol) in THF (100 mL) was added over 2 h in a pressure-equalized addition funnel to the above reaction mixture at 60° C. Toward the end of addition, the reaction mixture became a light pink clear solution. Stirring was continued at 60° C. for 18 h. After cooling to 0° C., 100 mL of 1.5 N HCl was added over 5 min. Then, the mixture was warmed to rt and stirred for 15 min. After separation, the organic layer was washed with brine (250 mL*2), dried over Na2SO4, filtered, and concentrated. The resulting material was suspended in acetonitrile (250 mL), stirred at rt for 1 h, and filtered to remove unreacted diacid starting material. Then, the filtrate was concentrated to approximately 125 mL. The resulting suspension was stirred at 0° C. for 2 h, becoming cloudier over time. The resulting solid was filtered, washed with cold (0° C.) acetonitrile (2*15 mL), and dried, affording 15-(tert-butoxy)-15-oxopentadecanoic acid (compound 1, 8.20 g, 25.0 mmol, 27.2percent yield) as an off white solid. NMR (400 MHz, CDCl3, ppm) delta 2.35 (t, J=7.58 Hz, 2H), 2.20 (t, J=7.46 Hz, 2H), 1.68-1.54 (m, 4H), 1.45 (s, 9H), 1.34-1.24 (m, 18H). 13C NMR (125 MHz, CDCl3, ppm) delta 179.91, 173.44, 79.93, 35.64, 34.08, 29.57, 29.48, 29.46, 29.41, 29.39, 29.29, 29.23, 29.09, 29.06, 28.12, 25.12, 24.70.
 

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