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[ CAS No. 333963-40-9 ] {[proInfo.proName]}

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Chemical Structure| 333963-40-9
Chemical Structure| 333963-40-9
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Product Details of [ 333963-40-9 ]

CAS No. :333963-40-9 MDL No. :MFCD08444045
Formula : C20H32F2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 390.46 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 333963-40-9 ]

* 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 [ 333963-40-9 ]

[ 333963-40-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 136790-76-6 ]
  • [ 333963-40-9 ]
YieldReaction ConditionsOperation in experiment
70% To a solution of compound 10 (150 g) in dichloromethane (15 volumes), was added 10% palladium on carbon (35% wt) and the suspension was hydrogenated at 2 PSI for 15 hours. After the completion of the reaction, the mixture was filtered through Celite, concentrated to near dryness and purified by column chromatography (ethyl acetate in hexanes) to give crude Lubiprostone. To a solution of crude Lubiprostone in ethyl acetate (10 vol) was added tert-butylamine (1.05 eq) at room temperature. The mixture was stirred at room temperature until precipitation of the amine salt occurred. The amine salt was isolated by filtration and dried to give Lubiprostone tert- butylamine salt (20 g). The amine salt was suspended in ethyl acetate (6 volumes) and water (3 volumes). The resulting bi-phasic mixture was adjusted to about pH 5 with formic acid. The organic layer was separated and concentrated to obtain Lubiprostone as a syrup. Upon crystallization using ethyl acetate/petroleum ether (1 :9 volumes), the syrup produced Lubiprostone(1 , 12 g) in approximately 70% recovery. The Lubiprostone filtrate was concentrated to near-dryness. HRMS (ESI+) [M + NH4]+ of (1): Formula: C20H36F2NO5: cal m/z: 408.25561 amu, found: 408.25626 amu .
  • 2
  • [ 32233-40-2 ]
  • [ 333963-40-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 1H-imidazole / dichloromethane / 15 h 1.2: 0 °C / pH 3 - 4 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C 2.2: 15 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C 4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / Inert atmosphere 5.2: 24 h 6.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C 6.2: 1 h / 20 °C 7.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 7.2: 3 h 8.1: Dess-Martin periodane / dichloromethane / 2 h 9.1: hydrogen / palladium 10% on activated carbon / dichloromethane / 15 h / 103.43 Torr 10.1: <i>tert</i>-butylamine / ethyl acetate / 20 °C 10.2: pH 5
Multi-step reaction with 14 steps 1.1: triethylamine; dmap / dichloromethane / 24 h / 20 °C / Inert atmosphere 1.2: 3 h / 20 °C 2.1: diisobutylaluminium hydride / toluene / 1 h / -75 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -5 °C / Inert atmosphere 3.2: 2 h / 0 °C / Inert atmosphere 4.1: triethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 20 °C / 760.05 Torr 6.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 7.1: dichloromethane / 6 h / 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 10.1: lithium hydroxide / tert-butyl methyl ether / 1 h / 20 °C / Inert atmosphere 10.2: 36 h / 45 °C 11.1: palladium 10% on activated carbon / water; ethyl acetate / 2 h / 20 °C 12.1: lithium hydroxide / tetrahydrofuran; water; ethanol / 2 h / 20 °C 13.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 14.1: phosphoric acid / water; acetonitrile / 2 h / 0 - 5 °C
Multi-step reaction with 10 steps 1.1: dmap; triethylamine / dichloromethane / 14 h / -5 - 25 °C 2.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 50 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C 5.1: lithium hydroxide monohydrate / tert-butyl methyl ether / 1 h / 20 °C / Inert atmosphere 5.2: 24 h / 45 °C 6.1: diisobutylaluminium hydride / toluene; hexane / 2 h / -78 °C / Inert atmosphere 6.2: 3 h / 20 °C / Inert atmosphere 7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0 °C 7.2: 0.83 h / 20 °C 8.1: palladium 10% on activated carbon; hydrogen / 2 h / 20 °C / 760.05 Torr 9.1: Dess-Martin periodane / dichloromethane / 14 h / 20 °C 10.1: phosphoric acid / acetonitrile; water / 2 h / 0 - 5 °C
Multi-step reaction with 9 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide; toluene / 6 h / 20 - 40 °C 1.2: 5 h / 130 °C 2.1: diisobutylaluminium hydride / toluene / 2 h / -22 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / Cooling with ice; Inert atmosphere 3.2: 3.17 h / Cooling with ice 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 45 °C 5.1: hydrogen; sodium hydroxide; 5%-palladium/activated carbon / acetonitrile; water / 18 h / 25 °C 6.1: potassium carbonate / acetone / 4 h / Reflux 7.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / Cooling with ice 8.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / 25 °C 8.2: 15 h 9.1: hydrogen; 20% palladium hydroxide-activated charcoal / isopropyl alcohol / 3 h / 25 °C

  • 3
  • [ 39746-00-4 ]
  • [ 333963-40-9 ]
  • 4
  • [ 74106-81-3 ]
  • [ 333963-40-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 °C / Inert atmosphere 1.2: 0.5 h / -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate / ethanol / 2 h / 20 °C 3.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4.1: 1H-imidazole / ethyl acetate 5.1: tert.-butyl lithium; copper(l) cyanide / diethyl ether; pentane / 0.5 h / -70 °C / Inert atmosphere 5.2: -70 - 0 °C / Inert atmosphere 6.1: formic acid; water / methanol / 3 h / 20 °C 7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; sodium hypochlorite / toluene; water / 0 °C 8.1: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 1 h
Multi-step reaction with 9 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 °C / Inert atmosphere 1.2: 0.5 h / -70 °C / Inert atmosphere 2.1: sodium tetrahydroborate / ethanol / 2 h / 20 °C 3.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4.1: 1H-imidazole / ethyl acetate 5.1: tert.-butyl lithium; copper(l) cyanide / diethyl ether; pentane / 0.5 h / -70 °C / Inert atmosphere 5.2: -70 - 0 °C / Inert atmosphere 6.1: formic acid; water / methanol / 3 h / 20 °C 7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; sodium hypochlorite / toluene; water / 0 °C 8.1: water; hydrogenchloride / acetonitrile / 1 h / 20 °C 9.1: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 3 h
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