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Chemical Structure| 439114-13-3 Chemical Structure| 439114-13-3
Chemical Structure| 439114-13-3

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CAS No.: 439114-13-3

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Product Details of Bis-PEG5-acid

CAS No. :439114-13-3
Formula : C14H26O9
M.W : 338.35
SMILES Code : O=C(O)CCOCCOCCOCCOCCOCCC(O)=O
MDL No. :MFCD11041120
InChI Key :VRTJBJNTMHDBAI-UHFFFAOYSA-N
Pubchem ID :18374596

Safety of Bis-PEG5-acid

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

Application In Synthesis of Bis-PEG5-acid

* 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 [ 439114-13-3 ]

[ 439114-13-3 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 41263-79-0 ]
  • [ 439114-13-3 ]
  • 2
  • [ 439114-13-3 ]
  • 3-[2-(2-{2-[2-(2-Chlorocarbonyl-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-propionyl chloride [ No CAS ]
  • 3
  • [ 112-60-7 ]
  • compound of BF3 with methanol [ No CAS ]
  • [ 439114-13-3 ]
  • 4
  • [ 439114-13-3 ]
  • 1-Dibenzo[b,f]azepin-5-yl-3-[2-(2-{2-[2-(3-dibenzo[b,f]azepin-5-yl-3-oxo-propoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-propan-1-one [ No CAS ]
  • 5
  • [ 439114-12-2 ]
  • [ 76-05-1 ]
  • [ 439114-13-3 ]
YieldReaction ConditionsOperation in experiment
In hydrogenchloride; dichloromethane; b) 3-[2-(2-{2-[2-(2-Carboxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propionic acid (40) A solution of tert-butyl 3-[2-(2-{2-[2-(2-tert-butoxycarbonylethoxy)ethoxy]ethoxy}-ethoxy)ethoxy]propionate 24 in 50 ml of methylene chloride and 50 ml of trifluoro-acetic acid is stirred for 2 h and then concentrated. The residue is taken up in 1N hydrochloric acid and extracted with methylene chloride. The organic phase is concentrated and contains 40. C14H26O9 (338.36) MS (ESI) 339 (M+H)
  • 6
  • [ 782475-32-5 ]
  • [ 439114-13-3 ]
  • [ 909008-17-9 ]
YieldReaction ConditionsOperation in experiment
32% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 1h; 3-(2-{2-[2-(2-{2-[2-(4-{2-[2-(2-Methyl-[1,3]dioxolan-2-ylmethyl)-[1,3]dioxolan-2-yl]-ethyl}-phenylcarbamoyl)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid Compound from EXAMPLE 20 (0.6 g, 1.8 mmol) was dissolved in dichloromethane (10 ml) and 4-{2-[2-(2-Methyl-[1,3]dioxolan-2-ylmethyl)-[1,3]dioxolan-2-yl]-ethyl}-phenylamine (0.3 g, 1.4 mmol) followed by EDCI (0.28 g, 1.8 mmol) was added at RT. After 1 hr at RT the RM was washed with water and dried over sodium sulfate. Evaporation of volatiles and purification over silica gel column with 1 to 15% methanol in dichloromethane provided title compound as gum (0.47 g, 32%).
32% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 1h; Compound from Example 20 (0.6 g, 1.8 mmol)was dissolved in dichloromethane (10 ml) and 4-{2-[2-(2-Methyl-[1,3]dioxolan-2-ylmethyl)-[1,3]dioxolan-2-yl]-ethyl}-phenylamine (0.3 g, 1.4 mmol) followed by EDCI (0.28 g, 1.8 mmol) was added at RT. After 1 hr at RT the RM was washed with water and dried over sodium sulfate. Evaporation of volatiles and purification over silica gel column with 1 to 15% methanol in dichloromethane provided title compound as gum (0.47 g, 32%).
  • 7
  • [ 439114-12-2 ]
  • [ 439114-13-3 ]
YieldReaction ConditionsOperation in experiment
82% With methoxybenzene; trifluoroacetic acid; at 0 - 20℃; for 3h; A solution of 3-{2-[2-(2-{2-[2-(2-tert-Butoxycarbonyl-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (6 g, 18.6 mmol) in anisole (20 ml) was cooled in an ice bath and trifluroacetic acid (65 g) was added. After 3 hrs at RT volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate (50 ml) and 5% sodium bicarbonate solution. The aqueous layer was acidified with 1 N HCl, saturated with NaCl and then extracted with ethyl acetate (3×50 ml). Combined organic layers were washed with brine and dried over sodium sulfate. Removal of volatiles under the reduced pressure provided the product as colorless liquid which solidified upon refrigeration (3.8 g, 82%).
82% A solution of 3-{2-[2-(2-{2-[2-(2-tert-Butoxycarbonyl-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (6 g, 18.6 mmol) in anisole (20 ml) was cooled in an ice bath and trifluoroacetic acid (65 g) was added. After 3 hrs at RT volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate (50 ml) and 5% sodium bicarbonate solution. The aqueous layer was acidified with 1 N HCl, saturated with NaCl and then extracted with ethyl acetate (3*50 ml). Combined organic layers were washed with brine and dried over sodium sulfate. Removal of volatiles under the reduced pressure provided the product as colorless liquid which solidified upon refrigeration (3.8 g, 82%).
  • 8
  • [ 4229-38-3 ]
  • [ 439114-13-3 ]
  • [ 1016647-07-6 ]
  • 9
  • [ 102039-77-0 ]
  • [ 439114-13-3 ]
  • [ 1016647-10-1 ]
  • 10
  • [ 309259-65-2 ]
  • [ 439114-13-3 ]
  • [ 1206805-28-8 ]
  • 11
  • C46H76N10O22Pol [ No CAS ]
  • [ 439114-13-3 ]
  • [ 1204530-93-7 ]
  • 12
  • C42H76N10O14Pol [ No CAS ]
  • [ 439114-13-3 ]
  • [ 1204531-01-0 ]
  • 13
  • C46H80N10O18Pol [ No CAS ]
  • [ 439114-13-3 ]
  • [ 1204530-97-1 ]
  • 14
  • C44H80N10O14Pol [ No CAS ]
  • [ 439114-13-3 ]
  • [ 1204531-02-1 ]
  • 15
  • C45H72N10O24Pol [ No CAS ]
  • [ 439114-13-3 ]
  • [ 1206805-27-7 ]
  • 16
  • [ 6066-82-6 ]
  • [ 439114-13-3 ]
  • C22H32N2O11 [ No CAS ]
  • 17
  • C19(13)C4H27(15)NO5 [ No CAS ]
  • C19(13)C5H27(15)NO6 [ No CAS ]
  • C15(13)C6H23(15)NO4 [ No CAS ]
  • [ 439114-13-3 ]
  • [ 76-05-1 ]
  • [13C3,15N1]-Fmoc-L-alanine-OH [ No CAS ]
  • FMOC U-[13C,15N] valine [ No CAS ]
  • (x)C2HF3O2*C14(13)C46H104(15)N10O25 [ No CAS ]
YieldReaction ConditionsOperation in experiment
[15N, 13C]-PEG4(IETAV)2 (SEQ ID NO: 16) (AB140) was synthesized using Fmoc-protected amino acids containing fully 15N, 13C-labeled amino acid atoms (Cambridge Isotope Laboratories, Inc., Andover, Mass., USA). Amino acid building blocks for Thr and Glu were side chain protected with tert-butyl groups. Labeled Fmoc-Val-OH (0.125 mmol, 43 mg) was dissolved in DMF (1.5 mL) and loaded to the 2-chlorotrityl chloride resin (0.1875 mmol, 119 mg) that had been swelled in DMF (2 mL) for 20 min and drained. DIPEA (0.625 mmol, 109 muL) was added and shaking was continued for 60 min. MeOH (100 muL) was added, and shaking was continued for 15 min, and the resin washed with DMF. Fmoc was removed with piperidein/DMF and labeled IETAV (SEQ ID NO: 16 ) was further synthesized using coupling conditions and stoichiometries of 1/2/2/3 of resin/Fmoc-amino acid/HATU/collidine in DMF (1 mL) for 40 min. After the final Fmoc-removal, the resin was washed with DMF and DCM, dried in vacuo and used further to prepare AB140 by the on-resin dimerization process with the (unlabeled) PEG4-diacid linker (IRIS Biotech, Marktredwitz, Germany) described previously (WO2010/004003).Synthesized compounds, including dimeric PSD-95 inhibitors and derivatives thereof, were obtained as TFA saltsby treating the resin-bound products with trifluoroacetic acid (TFA)/triisopropylsilane/H20 (90/5/5) for 2 hours (unless other specification is stated), evaporation in vacuo, precipitation with cold ether, lyophilization, and purification with preparative reverse phase high-performance liquid chromatography (RP-HPLC). Compounds were characterized byanalytical HPLC and mass spectrometry (Table 1).
  • 18
  • [ 439114-13-3 ]
  • C37H59N5O16 [ No CAS ]
  • 19
  • [ 439114-13-3 ]
  • C40H75N5O14 [ No CAS ]
  • 20
  • [ 1025796-31-9 ]
  • [ 439114-13-3 ]
  • C38H69N3O15 [ No CAS ]
  • 21
  • tert-butyl 4-{3-{3-methyl-5-[3-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-carbonyl)pyridin-4-oxy]-6-chlorobenzofuran-2-yl}acryloyl}piperazine-1-carboxylate [ No CAS ]
  • [ 439114-13-3 ]
  • 1,19-bis({4-[(E)-3-(3-methyl-5-[3-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)pyridin-4-yl]oxy}-6-chlorobenzofuran-2-yl)acryloyl]piperazin-1-yl})-4,7,10,13,16-pentaoxanonadecane-1,19-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% The 4 - {3 - {3 - methyl -5 - [3 - (4 - cyclopropyl - 1, 2, 3, 4 - tetrahydroquinoxaline -1 - carbonyl) pyridine -4 - oxy] -6 - chlorobenzene and furan -2 - yl} acryloyl} piperazine -1 - formic acid tert-butyl ester (300 mg, 0 . 43 mmol) dissolved in dichloromethane (9 ml), by adding 2 mol/L hydrochloric acid-ethyl acetate solution (1 ml), the reaction at room temperature for 2 hours, the reaction fluid evaporation, then adding dichloromethane (10 ml), 4, 7, 10, 13, 16 - five oxygen nonadecanes - 1, 16 - dicarboxylic acid (69 mg, 0 . 21 mmol), HATU (231 mg, 0 . 61 mmol), triethylamine (113 mul, 0 . 84 mmol), the reaction at room temperature overnight, water, dichloromethane is used for extraction, the organic layer drying, evaporation to dryness, the preparing of high performance liquid chromatography purification product 164 mg, yield is 52%.
  • 22
  • [ 7724-12-1 ]
  • [ 439114-13-3 ]
  • 19-((2-cyanobenzo[d]thiazol-6-yl)amino)-19-oxo-4,7,10,13,16-pentaoxanonadecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; To a flask containing 4,7,l0,l3,l6-pentaoxanonadecanedioic acid (0.695 g, 2.05 mmol) and 6-aminobenzo[
  • 23
  • [ 1448297-52-6 ]
  • [ 439114-13-3 ]
  • (S)-21-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carbonyl)-22,22-dimethyl-19-oxo-4,7,10,13,16-pentaoxa-20-azatricosanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; for 12h;Inert atmosphere; General procedure: To a stirred solution of succinic acid (680mg, 5.8mmol) in DMF (10mL) was added anhydrous DCM (150mL). Then the mixture was cooled to 0C, NMM (1.16g, 11.5mmol), VHL-1 (1.0g, 2.3mmol), HOAT (63mg, 0.46mmol) and EDCI.HCl (530mg, 2.8mmol) were added sequentially. The solution was purged and refilled with nitrogen. The resulting mixture was stirred at room temperature for 12h. The reaction mixture was quenched with water (1mL). After concentration, the residue was purified reverse phase ISCO (C18) to afford the desired compound s-4a (4-(((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid) (s-4a) (0.82g, 65% yield) as a white solid.
  • 24
  • [ 1448297-52-6 ]
  • [ 439114-13-3 ]
  • N-(2-chloro-6-methylphenyl)-2-((6-(4-((S)-21-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carbonyl)-22,22-dimethyl-19-oxo-4,7,10,13,16-pentaoxa-20-azatricosanoyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide [ No CAS ]
  • 25
  • [ 439114-13-3 ]
  • (2S,4R)-1-((S)-2-(tert-butyl)-22-(4-(4 -((5-chloro-4-((2-(dimethylphosphoryl)phenyl)amino)pyrimidine-2-yl)amino)-3-methoxyphenyl)piperazin-1-yl)-4,22-dioxo- 7,10,13,16,19-pentaoxa-3-azadocosanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide [ No CAS ]
  • 26
  • [ 439114-13-3 ]
  • N1-(1-(4-((5-chloro-4-((2-(dimethylphosphoryl)phenyl)amino)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidin-4-yl)-N19-((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-4,7,10,13,16-pentaoxanonadecanediamide [ No CAS ]
  • 27
  • [ 439114-13-3 ]
  • (2S,4R)-1-((S)-2-(tert-butyl)-22-(4-(1-(4-((5-chloro-4-((2-(dimethylphosphoryl)phenyl)amino)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidin-4-yl)piperazin-1-yl)-4,22-dioxo-7,10,13,16,19-pentaoxa-3-azadocosanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide [ No CAS ]
 

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