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Chemical Structure| 141282-24-8 Chemical Structure| 141282-24-8
Chemical Structure| 141282-24-8

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Product Details of Tr-peg6

CAS No. :141282-24-8
Formula : C29H36O6
M.W : 480.59
SMILES Code : OCCOCCOCCOCCOCCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
English Name :1,1,1-Triphenyl-2,5,8,11,14-pentaoxahexadecan-16-ol
MDL No. :MFCD30527390

Safety of Tr-peg6

Application In Synthesis of Tr-peg6

* 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 [ 141282-24-8 ]

[ 141282-24-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 4792-15-8 ]
  • [ 76-83-5 ]
  • [ 141282-24-8 ]
YieldReaction ConditionsOperation in experiment
72% In pyridine for 70h;
67% With triethylamine In dichloromethane at 20℃; for 4h;
50.9% With pyridine at 60℃;
46% With N,N-dimethyl-4-aminopyridine In N,N-dimethyl-formamide; toluene at 50℃; for 22h; 3 PEG5-di-OH (6) (n = 5) (5.88 g, 24.19 mmol) was dissolved in toluene (30 mL), and concentrated to remove toluene under reduced pressure. The residue was dried under high vacuum. Anhydrous DMF (40 mL) was added, followed by an addition of DMAP (0.91 g, 7.29 mmol) and TrCl (trityl chloride) (1.66 g, 5.84 mmol). The resulting mixture was heated at 50 0C for 22 hours. The reaction was concentrated to remove the solvents (high vacuum, 50 0C). The residue was mixed with water, and extracted with EtOAc (3 x 25 mL). The combined organic solution was washed with brine, dried over Na2CO3, concentrated. The residue was purified with flash column chromatography on silica gel to result in 1.29 g of product in 46 % yield. The product was confirmed with 1H-NMR in CDCl3.
With sodium hydroxide In tetrahydrofuran; lithium hydroxide monohydrate; benzene for 24h; Heating;
With N,N-dimethyl-4-aminopyridine In pyridine; chloroform P.5 Synthesis of 2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy) ethanol Synthesis of 2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy) ethanol Pentaethylene glycol (Compound 1; 10 g, 42.0 mmol) was dissolved in pyridine (100 ml), triphenylmethyl chloride (11.6 g, 41.6 mmol) and 4-dimethylaminopyridine (0.9 g, 7.4 mmol) were added at room temperature, and this was followed by overnight stirring at 35° C. This was concentrated under reduced pressure; the residue obtained was dissolved in chloroform, the organic phase was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, after which it was dried with sodium sulfate. The solid was removed by cotton filtration and washed with chloroform, and the filtrate and the washings were combined and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography (Kanto Chemical 60N; 600 ml) with an eluent (60:1 chloroform (CHCl3)-methanol (MeOH)) to yield the desired 2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)ethanol (Compound 2; 10.4 g, 51.2%). 1H-NMR(CDCl3) δ: 2.53 (1H, t), 3.16 (2H, t), 3.49-3.63 (18H, m), 7.14-7.41 (15H, m).
With pyridine In acetonitrile at 0 - 20℃; 3.1 Step 1. Synthesis of 16,16,16-triphenyl-3,6,9,12,15-pentaoxahexadecanol 10 g of pentaethyleneglycol was dissolved in a mixture of 100 mL of acetonitrile and 30 mL of pyridine, to which 11 g of trityl chloride were added at 0 °C, and then the solution was stirred overnight at room temperature. The reaction solution was mixed with iced water and subjected to extraction with ethyl acetate, and then the organic layer was washed with water and concentrated under reduced pressure after drying. The residue was purified with silica gel column chromatography to obtain 6 g of the objective compound.

  • 2
  • [ 108534-47-0 ]
  • [ 141282-24-8 ]
  • [ 675606-49-2 ]
YieldReaction ConditionsOperation in experiment
60% With tributylphosphine; diamide In toluene at 20℃;
  • 3
  • [ 16696-65-4 ]
  • [ 141282-24-8 ]
  • [ 1002323-05-8 ]
YieldReaction ConditionsOperation in experiment
61% With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h;
  • 4
  • [ 124-63-0 ]
  • [ 141282-24-8 ]
  • [ 1056881-14-1 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: methanesulfonyl chloride; 2-(2-{2-[2-(trityloxyethoxy)ethoxy]ethoxy}ethoxy)ethanol With triethylamine In dichloromethane at 0 - 20℃; for 16.5h; Stage #2: With water In dichloromethane 3 Methanesulfonyl chloride (0.35 mL, 4.48 mmol) was added dropwise to a stirred solution of TrO-PEG5-OH (8) (n = 5) (1.29 g, 2.68 mmol) and triethylamine (0.9 mL, 6.46 mmol) in dichloromethane (15 mL) at 0 0C. After the addition, the resulting solution was stirred at room temperature for 16.5 hours. Water was added to quench the reaction. The organic phase was separated and the aqueous solution was extracted with dichloromethane (10 mL). The combined organic solution was washed with brine (3 x 30 mL), dried over Na2SO4 and concentrated to afford the product as oil (1.16 g) in 78% yield. The product (8) (n = 5) was confirmed with 1H-NMR in CDCl3.
  • 5
  • [ 79-08-3 ]
  • [ 141282-24-8 ]
  • [ 635287-21-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(2-{2-[2-(trityloxyethoxy)ethoxy]ethoxy}ethoxy)ethanol With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: bromoacetic acid In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #3: With potassium hydrogensulfate; water In tetrahydrofuran; N,N-dimethyl-formamide 3.2 Step 2. Synthesis of 16,16,16-triphenyl-3,6,9,12,15-pentaoxahexadecoxybenzyl acetate ester 5.5 g of 16,16,16-triphenyl-3,6,9,12,15-pentaoxahexadecanol obtained in the above step 1 was dissolved in 30 mL of dimethylformamide, and then the solution was added dropwise to a suspension containing 2.3 g of sodium hydride in 100 mL of tetrahydrofuran at 0 °C. After stirring at room temperature for 30 minutes, the solution was again cooled at 0 °C, and then 3.5 g of bromoacetic acid was added. After stirring at room temperature for 2 hours, the reaction solution was mixed with 10 % potassium hydrogen sulfate solution and subjected to extraction with dichloromethane, and then the organic layer was washed with water and concentrated under reduced pressure after drying. 1.7 mL of benzyl alcohol, 2.4 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloric acid and 144 mg of 4-dimethylaminopyridine were added to the residue, and the solution was stirred overnight at room temperature in 50 mL of dichloromethane. The reaction solution was mixed with saturated sodium bicarbonate water, and then subjected to extraction with ethyl acetate. The organic layer was concentrated under reduced pressure after drying. The residue was purified with silica gel column chromatography to obtain 5.5 g of the objective compound.
  • 6
  • [ 141282-24-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / water / 0.67 h / 40 °C 2: N-benzyl-trimethylammonium hydroxide / dichloromethane / 24 h / 20 °C
  • 7
  • [ 141282-24-8 ]
  • [ 106-89-8 ]
  • [ 1453169-19-1 ]
YieldReaction ConditionsOperation in experiment
87% With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 40℃; for 0.666667h;
  • 8
  • [ 105589-77-3 ]
  • [ 141282-24-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 1.2: 12 h / 0 - 20 °C / Inert atmosphere 2.1: sulfuric acid; water / mineral oil; tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
  • 9
  • [ CAS Unavailable ]
  • [ 141282-24-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; water In tetrahydrofuran; mineral oil at 20℃; for 3h; Inert atmosphere;
  • 10
  • [ 141282-24-8 ]
  • [ 4792-15-8 ]
YieldReaction ConditionsOperation in experiment
13.31 g With toluene-4-sulfonic acid In methanol at 20℃; for 12h; Inert atmosphere;
 

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