630-580-1088 sales@ambeed.com
Structure Search

List Search MOL Search Structure Search

0
Chemistry
Asymmetric Synthesis >>Chiral Building BlocksChiral Catalysts, Chiral Ligands and Chiral ReagentsChiral Resolution ReagentsBoronic acids/esters >>Aliphatic BoronsAromatic BoronsOther BoronsOxaborolesCatalysis Chemistry >>Achiral Crown LigandsC-H ActivationCarbon-Donor LigandsChiral Carbon LigandsChiral Crown LigandsChiral Olefin LigandsCross-CouplingCross-Coupling Using Transition Metal CatalystsDACH or Trost LigandsChemical Biology >>Conjugation Chemistry
GlycoscienceLinkers and CrosslinkersNucleic Acid ChemistryPEGylationPeptide ChemistryPhotolabile Protecting GroupHeterocyclic Building Blocks >>AcridinesAliphatic HeterocyclesAromatic HeterocyclesAzetidinesBenzimidazolesBenzisoxazolesBenzodioxansBenzofuransBenzothiazolesInorganic reagents >>Inorganic reagentOrganic Building Blocks >>Acid AnhydridesAcyl Chlorides
AlcoholsAldehydesAliphatic Chain HydrocarbonsAliphatic Cyclic HydrocarbonsAlkenesAlkylsAlkynesOrganometallic Reagents >>Grignard ReagentsOrganoarsenicOrganobismuthOrganoboronOrganogermaniumOrganolithiumOrganomercuryOrganosiliconOrganotinSpecialty Synthesis >>Enzyme-Mediated SynthesisFluorous SynthesisIonic Liquids
Solid Supported SynthesisStains and Dyes >>Acid DyesAzoic DyesBasic DyesDirect DyesDisperse DyesDye IntermediatesMordant DyesOil DyesOther Stains and DyesSynthetic Reagents >>Acids and BasesC-C Bond FormationC-X Bond Formation (Halogen)C-X Bond Formation (Non-Halogen)Chelation and Complexation CompoundsCondensation AgentsCouplingDehydrating ReagentsFluorination Reagent
Pharmaceutical Intermediates
Analgesics >>BenzhydrocodoneBicifadineCapsaicinCelecoxibDebio-0827DexamethasoneElagolix SodiumEsketamine HydrochlorideIbuprofen sodiumAnesthetics >>CiprofolEsketamine HydrochlorideFospropofol Fospropofol DisodiumLevobupivacaine RemimazolamRemimazolam BesilateRemimazolam besylateRopivacaineAnti-Addiction Agents >>Kakonein
Lofexidine HydrochlorideVarenicline Anti-inflammatory Agents >>ApremilastAsunaprevirATB-346 RelatedBalsalazide BaricitinibBencycloquidium BromideBudesonideCefiderocol Sulfate TosylateCeftaroline Fosamil AcetateAntibacterials >>AFN-1252 RelatedAlatrofloxacin Bedaquiline FumarateBesifloxacin BrilacidinCaspofungin AcetateCefiderocol Sulfate TosylateCefilavancinCeftaroline Fosamil
Anticonvulsants >>BrivaracetamCannabidiolEscitalopram OxalateEslicarbazepine Acetate RelatedFosphenytoinGabapentin EnacarbilJNJ-10234094LacosamideLevetiracetam RelatedAntidementia Agents >>Azeliragon RelatedDavunetideDonepezil HydrochlorideDonepezil RelatedEnsaculinFlorbetaben Flortaucipir F 18Flutemetamol IdalopirdineAntidepressants >>4-Chlorokynurenine
AgomelatineAgomelatine RelatedAllopregnanolone RelatedAmibegronAmitifadineAripiprazole RelatedBasimglurantBefloxatoneAntiemetics >>AprepitantAprepitant RelatedDolasetron RelatedDolasetron Mesylate HydrateFosaprepitant DimeglumineFosaprepitant RelatedOlanzapinePalonosetron RelatedPalonosetron HydrochlorideAntifungals >>Anidulafungin RelatedCabotegravirMore >>
Inhibitors/Agonists
ADC >>ADC AntibodyADC LinkerADC Linker with PayloadADC ToxinAntibody-Drug Conjugates (ADCs)Drug-Linker Conjugates for ADCAngiogenesis >>ALKBcr-AblBTKEGFRFAKFGFRFLT3HER2HIFAnti-infection >>3CLproAntibacterialAntibioticAntifungal
AntiparasiticAntiprotozoalAntiviralArenavirusBVDVApoptosis >>Apoptosis InducerBcl-2Bcl-6BRKc-Mycc-RETC/EBPCARDCaspaseAutophagy >>Atg4ATG4BATTECsAUTACsAutophagyBeclin1
FKBPLC3LRRK2Biochemical Reagent >>Cell Cycle >>AntifolateAPCAurora KinaseBUBCasein KinaseCdc25CDKChkCRISPR/Cas9Cytoskeleton >>ActinArp2/3 ComplexCYTHCytoplasmic dyneinDynaminFAKMore >>
Material Science
Aggregation-Induced Emission >>Other AIE BlocksTetraphenylethylene SeriesCOFs Linkers >>Aldehyde COFs LinkersAlkynyl COFs LinkersAmine COFs LinkersBoric COFs LinkersCyano COFs LinkersMultifunctional COFs linkersOther COFs linkersTriphene seriesElectronic Materials >>Battery MaterialsDye-Sensitized Solar Cell (DSSC) MaterialsElectronic MaterialLiquid Crystal (LC) MaterialsMolecular ConductorsOrganic Light-Emitting Diode (OLED) MaterialsOrganic Solar Cell (OPV) MaterialsOrganic Transistor (OFET) MaterialsPerovskite Solar Cell (PSC) MaterialsMagnetic Materials >>Magnetic Ionic LiquidsMagnetic MaterialMagnetic Metal Complexes
Organic Radicals Material Chemical Compounds >>Ligands for Functional Metal ComplexesLiquid Crystal (LC) Building BlocksPhthalocyanine Building BlocksPolymer and Macromolecule Semiconductor Building BlocksSmall Molecule Semiconductor Building BlocksSolubility Enhancing Reagents Supramolecular Host Materials MOF Ligands >>Carboxylic Acid MOF LigandsCarboxylic Acid Nitrogen-Containing Mixed MOF LigandsNitrogen-Containing MOF LigandsOther MOF ligandsNanomaterials >>Carbon NanomaterialsCeramic MembranesDendrimersGold NanoparticlesIron Oxide NanoparticlesMaterials by ApplicationMesoporous MaterialsMetals and Metal AlloysNano Minerals: NanoclaysOLED Materials >>Dopant
HostHTMOLED IntermediatesOther OLED related materialsOptical Materials >>Coumarin DyesCyanine and Squarylium DyesDCM DyesDipyrromethene DyesFluorescence MaterialsFluorescent ProbesHeat and Pressure Sensitive DyesNear-Infrared (NIR) DyesOrganic Non-Linear Optical (NLO) MaterialsOrganic Pigments >>Organic PigmentOther Materials >>Mateial OtherPolymer Science >>MonomersPolymer AdditivesPolymerization ReagentsPolymersResins
Contact Us
Home Cart 0 Sign in  

[ CAS No. 126587-36-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 126587-36-8
Chemical Structure| 126587-36-8
Structure of 126587-36-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 126587-36-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 126587-36-8 ]

SDS Specification
Alternatived Products of [ 126587-36-8 ]

Product Details of [ 126587-36-8 ]

CAS No. :126587-36-8 MDL No. :MFCD26406818
Formula : C14H23NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 285.34 Pubchem ID :-
Synonyms :

Safety of [ 126587-36-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 126587-36-8 ]

* 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 [ 126587-36-8 ]

[ 126587-36-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 88738-78-7 ]
  • [ 95715-87-0 ]
  • [ 126587-36-8 ]
YieldReaction ConditionsOperation in experiment
85% With 18-crown-6 ether; sodium hydride at -78℃;
85% Stage #1: bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate With potassium hexamethylsilazane; 18-crown-6 complexed with acetonitrile In tetrahydrofuran; toluene at -78℃; for 0.25h; Inert atmosphere; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; toluene at -78 - 0℃; Inert atmosphere;
82% Stage #1: bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine With 18-crown-6 ether In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; enantioselective reaction; 2 (S,Z)-tert-Butyl 4-(3-methoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate (S,Z)-2 General procedure: To an oily suspension of NaH 60% (2.1g, 52.5mmol) in THF (90mL), at 0°C, under nitrogen was added, dropwise, a solution of (CF3CH2O)2P(O)CH2CO2Me (10mL, 52.3mmol) in THF (60mL). The solution was stirred at 0°C for 30min and then cooled to -78°C. To this solution was added 18-Crown-6 (69g, 261mmol) in THF (150mL) and then (R)-Garner’s aldehyde 1 (9.2g, 40.2mmol) in THF (20mL). The reaction mixture was stirred at the same temperature for 2h and the reaction quenched with aqueous saturated NH4Cl solution. The reaction mixture was extracted with Et2O, dried over MgSO4, and concentrated under vacuum. The crude residue was purified by column chromatography (silica gel, hexanes/Et2O:(1/4)) to give product (S,Z)-2 as white solid. Yield (9.39g, 82%). TLC (hexane/Et2O:1/1): Rf=0.71. HPLC (CH3CN/H2O:50/50, 0.7mL/min): tR=9.5min. 1H NMR (250MHz, CDCl3) δ (ppm) 6.22 (m, 1H, CH=CH-COOMe), 5.78 (d, 3JH-H=11.4Hz, 1H, CH=CH-COOMe), 5.34 (s, 1H, CH-α), 4.23 (t, 3JH-H=7.8Hz, 1 H, CH2aO), 3.71 (dd, 3JH-H=9.2 and 4JH-H=3.1Hz, 1H, CH2bO), 3.65 (s, 3H, COOCH3), 1.57 (s, 3H, C-CH3), 1.50-1.22 (m, 12H, C-CH3 and [C(CH3)3] Boc). 13C NMR (63MHz, CDCl3) δ (ppm) 166.25 (COOMe), 152.26 (CO Boc), 151.86/151.24 (rotamers, CH=CH-COOMe), 119.67/119.08 (rotamers, CH=CH-COOMe), 94.42/93.89 (rotamers, C-(CH3)2), 80.54/79.92 (rotamers, ([C(CH3)3]Boc), 69.03/68.80 (rotamers, CH2O), 56.61/55.58 (rotamers, CH-α), 51.38 (COOCH3), 28.34 ([C(CH3)3] Boc), 27.32/26.62 (rotamers, C-CH3), 24.92/23.75 (rotamers, C-CH3). The enantiomeric excess of (S,Z)-2 was determined by HPLC (Chiral OD-H column, i-PrOH/hexane:5/95), tR=7.8min for (R) enantiomer and tR=8.5min for (S) enantiomer in the HPLC chromatogram. The ee for (S,Z)-2 was 94% and its [α]25D[α]D25 -27.3 (c=0.91, CHCl3). For (R,Z)-2 enantiomer the ee=96% and the measured [α]25D[α]D25 +28.5 (c=1.03, CHCl3). LRMS-(ESI+), m/z: 286.2 [M+H]+, 308.1 [M+Na]+.
81% With 18-crown-6 ether; sodium hydride In tetrahydrofuran
72% Stage #1: bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate With 18-crown-6 ether; potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran at -78℃; for 3h;
With 18-crown-6 ether; potassium hydride; 1,1,1,3,3,3-hexamethyl-disilazane THF, -78 deg C; Yield given. Multistep reaction;
With 18-crown-6 ether; potassium hydride; 1,1,1,3,3,3-hexamethyl-disilazane 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min; Yield given. Multistep reaction;
With sodium hydride 1.)THF, 0 deg C, 30 min 2.) THF, -78 deg C, 2 h; Yield given. Multistep reaction;

Reference： [1]Shimamoto, Keiko; Ohfune, Yasufumi [Tetrahedron Letters, 1990, vol. 31, # 28, p. 4049 - 4052]
[2]Location in patent: experimental part Spangenberg, Thomas; Schoenfelder, Angele; Breit, Bernhard; Mann, Andre [European Journal of Organic Chemistry, 2010, # 31, p. 6005 - 6018]
[3]Gahungu, Mathias; Arguelles-Arias, Anthony; Fickers, Patrick; Zervosen, Astrid; Joris, Bernard; Damblon, Christian; Luxen, André [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 4958 - 4967]
[4]Spangenberg, Thomas; Schoenfelder, Angele; Breit, Bernhard; Mann, Andre [Organic Letters, 2007, vol. 9, # 20, p. 3881 - 3884]
[5]Risgaard, Rune; Nielsen, Simon D.; Hansen, Kasper B.; Jensen, Christina M.; Nielsen, Birgitte; Traynelis, Stephen F.; Clausen, Rasmus P. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 4071 - 4081]
[6]Yanagida, Miwa; Hashimoto, Kimiko; Ishida, Michiko; Shinozaki, Haruhiko; Shirahama, Haruhisa [Tetrahedron Letters, 1989, vol. 30, # 29, p. 3799 - 3802]
[7]Hashimoto, Miwa; Hashimoto, Kimiko; Shirahama, Haruhisa [Tetrahedron, 1996, vol. 52, # 6, p. 1931 - 1942]
[8]Shimamoto, Keiko; Ohfune, Yasufumi [Journal of Medicinal Chemistry, 1996, vol. 39, # 2, p. 407 - 423]
  • 2
  • [ 108149-63-9 ]
  • [ 126587-36-8 ]
Reference： [1]Tetrahedron,1996,vol. 52,p. 1931 - 1942
[2]Tetrahedron Letters,1989,vol. 30,p. 3799 - 3802

Tags: 126587-36-8 synthesis path| 126587-36-8 SDS| 126587-36-8 COA| 126587-36-8 purity| 126587-36-8 application| 126587-36-8 NMR| 126587-36-8 COA| 126587-36-8 structure

Same Skeleton Products
Related Products
Historical Records