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[ CAS No. 756526-04-2 ] {[proInfo.proName]}

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Chemical Structure| 756526-04-2
Chemical Structure| 756526-04-2
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Product Details of [ 756526-04-2 ]

CAS No. :756526-04-2 MDL No. :MFCD11041146
Formula : C19H39NO10 Boiling Point : -
Linear Structure Formula :- InChI Key :YLKOHZCQTVYVDB-UHFFFAOYSA-N
M.W : 441.51 Pubchem ID :51340929
Synonyms :
Chemical Name :1-Amino-3,6,9,12,15,18,21,24-octaoxaheptacosan-27-oic acid

Safety of [ 756526-04-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 756526-04-2 ]

* 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 [ 756526-04-2 ]

[ 756526-04-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 756526-04-2 ]
  • [ 42014-51-7 ]
  • [ 1283658-79-6 ]
YieldReaction ConditionsOperation in experiment
With diisopropyl-carbodiimide; In dichloromethane; at 20℃; for 2h; 3.3. Preparation of 3-{2-r2-(2-{2-r2-(2-{2-r2-(3-bromo-propionylamino)-ethoxy1-ethoxy}- ethoxy)-ethoxy1-ethoxy>-ethoxy)-ethoxy1-ethoxy>-propionic acid 2,5-dioxo-pyrrolidin-1 -yl ester :Under magnetic stirring at RT, 100 mg of 3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)- propionic acid (CA(PEG)4, Pierce), 2 ml of DCM and 53.5 mg of bromo-acetic acid 2,5-dioxo- pyrrolidin-1-yl ester are successively introduced in a glass vial. After 1 hr at RT, 35.1 muIota of DIC are added. After 1 hr, the crude reaction medium is filtered on sintered glass, concentrated to dryness under RP, dilute with 10 ml of AcOEt, filtered on sintered glass and concentrated to dryness under RP. 76.5 mg of 3-{2-[2-(2-{2-[2-(2-{2-[2-(3-bromo-propionylamino)-ethoxy]-ethoxy}-ethoxy)- ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester are obtained in the form of a colourless oil. Mass spectra (A) : RT= 0.80 min ; [M+H]+ : m/z 659/661 ; [M- H+HC02H]- : m/z 703/705
  • 2
  • [ 67-56-1 ]
  • [ 756526-04-2 ]
  • [ 42014-51-7 ]
  • [ 1283658-88-7 ]
YieldReaction ConditionsOperation in experiment
10.2. Preparation of 3-r2-(2-{2-r2-(2-bromo-acetylamino)-ethoxy1-ethoxy>-ethoxy)-ethoxy1-Molecular Weight =400.27Molecular Formula =C14H26BrN07Under magnetic stirring, at RT, 100 mg of 3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)- propionic acid (CA(PEG)4, Pierce), 89 mg of bromo-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester and 2 ml of DCM are successively introduced in a glass vial. After 1 hr at RT, 0.7 ml of MeOH and 0.38 ml of a 2 M trimethylsilydiazomethane solution in hexane are added. After 1 hr at RT, the crude reaction mixture is concentrated to dryness under RP, then diluted with a minimum amount of DMA and purified by flash chromatography on C18-grafted silica gel (Merck, C18, 5g, 25-40 muiotatauiota, 18 ml/min, gradient of elution water:acetonitrile 100:0 to 5:95 by volume). After concentration of fractions containing the expected compound under RP, 58 mg of 3-[2-(2-{2-[2-(2-bromo- acetylamino)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-propionic acid methyl ester are obtained in the form of a colourless oil. Mass spectra (A) : tR = 0.75 min ; [M+H]+ : m/z 400/402
  • 3
  • [ 67-56-1 ]
  • [ 756526-04-2 ]
  • [ 42014-51-7 ]
  • [ 1283659-02-8 ]
YieldReaction ConditionsOperation in experiment
13.2. Preparation of 3-{2-r2-(2-{2-r2-(2-{2-r2-(2-bromo-acetylamino)-ethoxy1-ethoxy}-ethoxy- ethoxy1-ethoxy}-ethoxy)-ethoxy1-ethoxy}-propionic acid methyl esterUnder magnetic stirring, under an inert atmosphere of Ar, at RT, 200 mg of 3-[2-(2-{2-[2-(2-{2-[2- (2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-propionic acid (CA(PEG)8, Pierce), 1.7 ml of DCM, 0.9 ml of MeOH, and 0.34 ml of a 2M trimethylsilydiazomethane solution in hexane are successively introduced in a glass vial. After 30 min at RT, 0.1 ml of a 2M trimethylsilydiazomethane solution in hexane are added. After 25 min at RT, reaction mixture is neutralized by addition of a few drops of acetic acid, concentrated to dryness under RP, azeotroped with toluene. The so obtained colourless oil is diluted with a solution of 106.9 mg of bromo-acetic acid 2,5-dioxo-pyrrolidin-1 -yl ester in 0.7 ml of DCM. After 30 min at RT and 16 hrs at 4C, the crude is purified by flash-chromatography on 20 g CN-grafted silica gel (gradient of elution n.heptane/iPrOH/AcOEt with increasing iPrOH portion). After concentration of fractions containing the expected compound under RP, 175 mg of 3-{2-[2-(2-{2- [2-(2-{2-[2-(2-bromo-acetylamino)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]- ethoxy}-propionic acid methyl ester are obtained in the form of a colourless oil. Mass spectra (B) : tR = 2.79 min ; [M+H]+ : m/z 576/578.
  • 4
  • [ 756526-04-2 ]
  • [ 1426827-79-3 ]
  • C30H51NO12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; water; at 20℃; for 1.5h; To a solution of H2N-PEG8-COOH (822 mg, 1.86 mmol) in THF:H20 1 : 1 (20 mL) were added BCN-OSu (23) (651 mg, 2.23 mmol) and Et3N (774 μ, 5.59 mmol). The reaction was stirred at r.t. for 1.5 h andd acidified to pH 1 followed by extraction with EtOAc (3 x 35 mL). The combined organic layers were dried over Na2S04, filtered and the solvent removed under reduced pressure. The crude product was then dissolved in dry DCM (20 mL) and subsequently DCC (461 mg, 2.23 mmol) and NHS (257 mg, 2.23 mmol) were added. After stirring at r.t. for 1 h, the reaction was filtered and the filtrate concentrated in vacuo. Flash chromatography (MeCN, MeCN:H20 30: 1) afforded BCN-PEG8-COOSu.1H-NMR (300 MHz, CDC13): δ 5.44 (br s, 1H), 4.14 )d, J= 8.1 Hz, 2H), 3.84 (t, J= 6.3 Hz, 2H), 3.68-3.63 (m, 30H), 3.56 (t, J = 5.2 Hz, 2H), 3.34 (q, J = 5.4 Hz, 2H), 2.90 (t, J = 6.3 Hz, 2H), 2.85 (s, 4H), 2.36-2.14 (m, 6H). 1.72-1.49 (m, 2H), 1.36 (qn, J = 8.7 Hz, 1H), 1.02-0.88 (m, 2H).LRMS (ESI+) calcd for C34H54N2Oi4(M+Na+) 737.35, found 737.3.
  • 5
  • [ 756526-04-2 ]
  • [ 133081-25-1 ]
  • 3-[2-(2-{2-[2-(2-{2-[2-(2-{6-[(tert-butyl )-2-carboxyhydrazino]nicotinoylamino}ethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Preparation of 3-[2-(2-{2-[2-(2-{2-[2-(2-{6-[(tert-Butyl )-2-carboxyhydrazino]- nicotinoylamino}ethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propionic acid (BIL1)N-Boc 4-hydrazino nicotinic acid, NAG9, (0.38 g, 1 .50 mmol) was activated with TBTU (0.48 g, 1 .50 mmol), HOBt (0.23 g, 1 .50 mmol), and D IEA (0.39 g, 3.00 mg) in DMF (10 mL). After 20 min, a solution to Peg8 amino acid (0.44 g, 1 .00 mmol) was added, and the reaction was stirred for 1 h at room temperature. The reaction mixture was concentrated in vacuo and purified by Si02 chromatography with 5% MeOH in DCM to afford BIL1 (0.39 g, 58% yield). ESI MS+ mass calculated C3oH72N4013: 676.4, Found: 677.0 [M+H]+.
  • 6
  • [ 6066-82-6 ]
  • [ 756526-04-2 ]
  • [ 1426827-79-3 ]
  • [ 1608140-48-2 ]
YieldReaction ConditionsOperation in experiment
60% To a solution of amino-dPEG8-acid (217 mg, 0.492 mmol) in anhydrous DMF (3 mL) were subsequently added 51 (143 mg, 0.492 mmol) and Et3N (204 tL, 1.47 mmol). The reaction mixture stirred for 3h at rt, after which EDCI.HC1 (0.88 g, 4.61 mmol) and NHS (88 mg, 0.77 mmol) were added. The resulting solution was stirred overnight at rt andpoured into 50 mL NaHCO3 (sat.) and 50 mL EtOAc. The layers were separated and the organic phase was washed with sat. NaHCO3 (50 mL) and H20 (30 mL). The organic phase was dried (Na2504), filtered and concentrated in vacuo. Gradient flash chromatography (MeCN - MeCN:H20 30:1) afforded product 60b as colorless oil (212 mg, 0.30 mmol, 60%).‘H NMR (300 IVIFIz, CDC13): (ppm) 4.13 (d, J 8.1 Hz, 2H), 3.84 (t, J 6.3 Hz, 2H),3.68-3.59 (m, 28 H), 3.54 (t, J 5.1 Hz, 2H), 3.36 (q, J= 5.4 Hz, 2H), 2.89 (t, J= 6.3Hz, 2H), 2.82 (s, 4H), 2.35-2.15 (m, 6H), 1.68-1.48 (m, 2H), 1.44-1.23 (m, 1H), 1.00-0.86 (m, 2H). LRMS (ESI+) m/z calcd for C34H54N20,4 (M+Naj = 737.8; found 737.3.
  • 7
  • [ 756526-06-4 ]
  • [ 756526-04-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 60.0℃; for 8.0h; 30g of the amino end product obtained in step (3) was added to 100ml of 2M hydrochloric acid,Warmed to 60 C,Stir for 8h.The reaction is over,Adjust PH neutral,Then spin dry,Suction filtration,The filtrate was dried over anhydrous sodium sulfate,Spin dry,25 g of pure product was obtained.NMR data are as follows:
  • 8
  • [ 5117-19-1 ]
  • [ 756526-04-2 ]
  • 9
  • [ 125274-16-0 ]
  • [ 756526-04-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 1.3: 2 h / 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 °C / Inert atmosphere 2.2: 48 h / 20 °C / Inert atmosphere 3.1: Jones reagent / acetone / 0.75 h / 20 °C / Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 20 °C / 750.08 Torr
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere 1.2: 20 h / 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere 2.2: 48 h / 0 - 20 °C / Inert atmosphere 3.1: Jones reagent / acetone / 0.75 h / 20 °C / Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 20 °C / 750.08 Torr
  • 10
  • [ 756526-04-2 ]
  • [ 4105-92-4 ]
  • C32H51NO15 [ No CAS ]
  • C51H88N2O24 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 19% 2: 31% Stage #1: triethyl benzene-1,3,5-tricarboxylate With C72H117N4O44P3(6-)*6Na(1+); HATU In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-amino-3,6,9.12,15,18,21,24-octaoxaheptacosan-27-oic acid In N,N-dimethyl-formamide at 0 - 20℃; for 5h; 3.2.2. (3,5-Diethoxycarbonyl-1-benzenecarbonyl)-CA-PEG16 (14) Diethyl 1,3,5-benzenetricarboxylate (11, 526 mg, 1.97 mmol) was dissolved in anhydrousDMF (15 mL) under N2, HATU (951 mg, 2.50 mmol) added and the mixture cooledto 0 C. DIPEA (0.89 mL, 5.2 mmol) was then added and the mixture stirred for 30 min.CA-PEG8 (12, 1.00 g, 2.27 mmol) was then added and the mixture allowed to warm tor.t. over 5 h. The mixture was then evaporated to dryness and the residue purified byprep RP-HPLC using 40% MeCN/water containing 0.1% TFA as the mobile phase. Twocolourless oils were obtained after collection and evaporation: peak A at retention time12.2 min and peak B with retention time 12.8 min. Peak A was identified as compound 14(407 mg, 0.37 mmol, 19%) and peak B as compound 13 (422 mg, 0.61 mmol, 31%). Data for13 as described above. Data for 14: 1H-NMR (400 MHz, D2O) δH 8.21 (s, 2H, 2 phenylCH), 8.19 (s, 1H, phenyl CH), 4.21 (q, J = 7.1 Hz, 4H, 2 OCH2CH3), 3.65-3.35 (m, 64H,OCH2CH2), 3.20 (t, J = 6.0 Hz, 2H, CH2CO2H), 2.45 (t, J = 6.2 Hz, 2H, CH2NHCO), 2.35 (t,J = 6.2 Hz, 2H, CH2N), 1.22 (t, J = 7.1 Hz, 6H, 2 OCH2CH3) ppm; 13C-NMR (100.62 MHz,D2O) δC 175.97, 173.96, 167.45, 166.12, 134.41, 132.59, 132.06, 130.74, 69.55, 69.40, 68.77,66.70, 66.11, 62.73, 39.73, 38.94, 35.91, 34.25, 13.43; HR ES-MS m/z calcd for C51H88N2O24[M + H]+ 1112.5727, found 1112.5745.
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