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Chemical Structure| 14464-32-5 Chemical Structure| 14464-32-5

Structure of 14464-32-5

Chemical Structure| 14464-32-5

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Product Details of [ 14464-32-5 ]

CAS No. :14464-32-5
Formula : C22H39NO4
M.W : 381.55
SMILES Code : CCCCCCCCCCCCCCCCCC(ON1C(CCC1=O)=O)=O
MDL No. :MFCD00050403
InChI Key :ZERWDZDNDJBYKA-UHFFFAOYSA-N
Pubchem ID :3552761

Safety of [ 14464-32-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 14464-32-5 ]

* 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 [ 14464-32-5 ]

[ 14464-32-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 14464-32-5 ]
  • [ 498-63-5 ]
  • stearoyl-prolinol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine; at 20℃; for 72h; To a solution of stearic acid (0.5g 1.758mmol) in 5 ml dry pyridine (kept over KOH) (0.399g, 1.93mmol) and NHS (0.223 g, 1.93mmol) were added and dissolved in, stirred for 24hr at room temperature. Reaction was followed by TLC 5percent MeOH. Prolinol (0.197g, 1.949mmol) were added and the mixture was stirred at room temperature for three days was added to the mixture, and stirred at room temperature. Reaction <n="67"/>controlled by TLC (100percent Ethyl acetate). At the end of the reaction, volatiles were removed under reduced pressure and the mixture was dissolved in 30 ml DCM and DCU precipitate was filtrated off and the desired product was purified using column chromatography (ethyl acetate/DCM = 1:1). Yield:1H-NMR(CDCl3, delta ppm):4.24(42^,3.67(^1^,3.51(1,2^,2.30(1,2^,2.04^,2^,1.88(^2^,1.65^,2^,1.27^,28H),0.88(t,3,H)
  • 2
  • [ 14464-32-5 ]
  • [ 4089-07-0 ]
  • [ 1426701-66-7 ]
YieldReaction ConditionsOperation in experiment
86% General procedure: Lauric acid (12.0 g, 60 mmol) dissolved in dry ethyl acetate (100 mL) was added to a solution of N-hydroxysuccinimide (NHS) (6.9 g, 60 mmol) and N,N?-dicyclohexylcarbodiimide (DCC) (12.4 g, 60 mmol) in dry ethyl acetate (300 mL). The reaction mixture was left overnight at room temperature. Dicyclohexylurea (DCU) was removed by filtration and the filtrate was evaporated under reduced pressure to yield white crystals (17.4 g, 95 percent yield). Recrystallization from ethanol yielded 16.6g of pure dodecanoic acid 2,5-dioxo-pyrrolidine-1-yl ester. Tyrosine ethyl ester hydrochloride (TEEH) (12.6 g, 51 mmol) was dissolved in dry chloroform (300 mL) and neutralized by addition of triethylamine (TEA) (10 mL). To this solution was added dry dodecanoic acid 2,5-dioxo-pyrrolidine-1-yl ester (15.2 g, 51 mmol) and the reaction mixture was stirred for 24 h at room temperature. Solvent was evaporated under reduced pressure. Residue was dissolved in methylene chloride (300 mL) and the solution was washed with aqueous citric acid solution. Organic solvent layer was separated, dried over MgSO4 and then evaporated to dryness to obtain the white crystalline solid, the tyrosine-lauramide conjugate (Tyr-Lau), which was further purified by silica column chromatography (EtOAc/n-Hexane 2:3). Yield: 96 percent.
  • 3
  • [ 14464-32-5 ]
  • [ 29390-67-8 ]
  • mono[6-deoxy-6-(octadecanamido)]-β-cyclodextrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 45℃; for 18h; General procedure: Mono-6-amino-6-deoxy-beta-CD was prepared from the mono-6-O-p-toluenesulfonyl-beta-CD [36].Mono-6-amino-6-deoxy--CD (50 mg, 45 mumol) was added to NHS esters of stearic acid and oleic acid(36 mg, 90 mumol) in 1 mL of DMSO. The mixture was stirred for 18 h at 45 °C and then purified using flash chromatography (n-propyl alcohol: methanol: ethyl acetate = 7:3:3). The chemical structures ofthe fatty amido-beta-CDs were determined by MALDI-TOF spectrometry and NMR spectroscopy.
 

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[ 14464-32-5 ]

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Related Parent Nucleus of
[ 14464-32-5 ]

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