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CAS No. :19249-03-7 MDL No. :MFCD00048096
Formula : C20H26O8S2 Boiling Point : -
Linear Structure Formula :- InChI Key :KCONMNWPRXAWKK-UHFFFAOYSA-N
M.W : 458.55 Pubchem ID :316652
Synonyms :
Bis-Tos-PEG3

Safety of [ 19249-03-7 ]

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

Application In Synthesis of [ 19249-03-7 ]

* 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.

  • Upstream synthesis route of [ 19249-03-7 ]
  • Downstream synthetic route of [ 19249-03-7 ]

[ 19249-03-7 ] Synthesis Path-Upstream   1~8

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  • [ 19249-03-7 ]
YieldReaction ConditionsOperation in experiment
99% With potassium hydroxide In dichloromethane at 0 - 10℃; for 3 h; General procedure: Compounds 2a–c were prepared by a modified procedure known from the literature1. Oligo ethylene glycol(37.7 mmol) and p-toluenesulfonyl chloride (14.4 g, 75.4 mmol, 2 equiv) were dissolved in dichloromethane (36 mL)and this solution was cooled to 0 °C. During permanent stirring, milled potassium hydroxide (17 g, 302 mmol, 8equiv) was added and the solution was then stirred for 3 hours while the temperature was kept from 0 to 10 °C. This reaction was monitored by TLC (UV detection). After warming up to room temperature the reaction mixture was diluted by chloroform and extracted with water (3 × 1:1). Chloroform extracts were collected, dried over magnesium sulfate overnight, filtered and solvents were evaporated under reduced pressure.
96% With potassium hydroxide In dichloromethane at 0℃; for 5 h; Triethylene glycol (2.25 g, 15 mmol) and p-toluenesulfonyl chloride (5.72 g, 30 mmol)Dissolved in 15 ml of anhydrous dichloromethane, cooled to 0 ° C, fractionated under stirring,A small amount of KOH (6.72 g, 120 mmol) was added and the temperature was maintained at 0 ° C. After stirring at 0 ° C for 5 h,The reaction was quenched by the addition of 15 ml of dichloromethane and 30 ml of ice water. Separating the organic layer,The aqueous layer was extracted twice with 15 ml of dichloromethane, the combined organic layers were washed and washed once with 10 ml of water,After drying over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure to give 6.6 g of the title compound as a white solid, yield 96percent.
94%
Stage #1: With triethylamine In dichloromethane at 20℃; for 0.333333 h;
Stage #2: With dmap In dichloromethane at 20℃; for 16 h;
To solution of triethylene glycol (3.0 g, 20.0 mmol) in dichloromethane (20 mL) was added Et3N (6.06 g, 60.0 mmol) and reaction mixture was stirred at R.T. for 20 min. To reaction mixture were added p-toluene sulfonyl chloride (7.62 g, 40.0 mmol) and DMAP (0.12 g, 1 mmol), reaction mixture was stirred at room temperature for 16 hrs. Solvent was evaporated under vacuum, residue obtained was dissolved in ethyl acetate. Ethyl acetate layer was washed with 1N-HCl, brine and dried over Na2SO4. Organic layer was concentrated and purified on flash column to obtained (ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate) (5A) in 94 percent yield (8.58 g). 1H NMR (400 MHz, DMSO-d6) δ 7.81 (d, J = 8.2 Hz, 4H), 7.50 (d, J = 7.8 Hz, 4H), 4.13 (t, J = 4.3 Hz, 4H), 3.57 (t, J = 4.3 Hz, 4H), 3.41 (s, 4H), 2.45 (s, 6H); 13C NMR (100 MHz, DMSO-d6) δ 145.44, 132.89, 130.67, 128.15, 70.47, 70.08, 68.40, 21.61
92% With triethylamine In dichloromethane at 20℃; for 2 h; To a solution of triethylene glycol (750 mg, 1.0 equiv.) in DCM (20 mL) was added triethylamine (2.1 mL, 3.0 equiv.) then tosyl chloride (2.29 g, 2.4 equiv.) portion- wise and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was washed with saturated NH4C1 solution (20 mL x 3), then by brine. The resulting mixture was subsequently dried and evaporated. The residue was purified using flash column in the eluent of ethyl acetate/hexane (1/5, then 1/1) to give a white powder (2.11 g, 92percent). 1H NMR (500 MHz, DMSO) δ 7.77 (d, J = 8.0 Hz, 4H), 7.46 (d, J = 8.0 Hz, 4H), 4.09 (t, 4H), 3.53 (t, 4H), 3.38 (t, 4H), 2.41 (s, 6H); 13C NMR (125 MHz, DMSO) δ 145.3, 132.9, 130.6, 128.1, 70.4, 70.0, 68.3, 21.5; LCMS found m/z 459.5: (M+l).
91.4% With sodium hydroxide In tetrahydrofuran; water at 5℃; for 2 h; Large scale 16 kg (400 mol) of sodium hydroxide was dissolved in 80 L of water in a 400 L reactor, and then 18.8 L (140 mol) of triethylene glycol, 32 L of THF were added intothe reactot Afier cooling below 5° C., a solution of 47.84 kg(260 mol) of tosyl chloride and 50 L of THF was added dropwise. Following the addition, the reaction mixture waskept at this temperature for 2 hours, and it was then poured into 240 L of ice watet The precipitate was formed andfiltered, washed with a small amount of water, and dried.58.64 kg ofBPI-01 as a white crystalline powder was yielded at 91.4percent. mp: 77-80° C., HPLC: 97percent. TLC (petroleum ether:ethyl acetate=1:1) Rf=0.87.NMR data: ‘H-NMR (CDC13): ö ppm: 7.78 (d, 4H, J=10.4 Hz, benzene protons by sulfonyl group); 7.34 (d, 4H, J=1 1.6Hz, benzene protons by methyl group); 4.129 (dd, 4H, J=5.6Hz, ethylene protons by the sulfonyl group); 3.64 (dd, 4H,J=5.6 Hz, ethylene protons away from the sulfonyl group); 3.5 17 (s, 4H, ethylene protons in the middle); 2.438 (s, 6H, methyl protons on the benzene).
91.4% With sodium hydroxide In tetrahydrofuran; water at 5℃; for 2 h; Large scale Preparation: 16 kg (400 mol) of sodium hydroxide was dissolved in 80 L of water in a 400 L reactor, and then 18.8 L (140 mol) of triethylene glycol, 32 L of THF were added into the reactor. After cooling below 5° C., a solution of 47.84 kg (260 mol) of tosyl chloride and 50 L of THF was added dropwise. Following the addition, the reaction mixture was kept at this temperature for 2 hours, and it was then poured into 240 L of ice water. The precipitate was formed and filtered, washed with a small amount of water, and dried. 58.64 kg of BPI-01 as a white crystalline powder was yielded at 91.4percent. mp: 77-80° C., HPLC: 97percent. TLC (petroleum ether:ethyl acetate=1:1) Rf=0.87.
90% With potassium hydroxide In dichloromethane for 8 h; Cooling with ice The 10mL (0.075mol) of triethylene glycol,300ml dichloromethane,28.6g (0.15mol) of methyl chloride was added 500ml round-bottomed flask,Under ice-cooling,Was slowly added 33.6g (0.6mol) of potassium hydroxide,8h the reaction is substantially complete.The reaction solution was washed three times with water (3 × 100ml),The organic layer was collected,Dried over anhydrous sodium sulfate.filter,Spin dry solvent,The crude product was recrystallized from methanol,To give a white solid 30g,The yield was 90percent.
90.1% With dmap; triethylamine In dichloromethane at 20℃; for 3.5 h; Cooling with ice 434 mg of triethylene glycol (2.9 mmol) was dried in an oven at 95 ° C for 2 hours,Was dissolved in 43.5 mL of dichloromethane,1.06 g of 4-dimethylaminopyridine (8.7 mmol) and 400 μL of triethylamine (2.9 mmol)1.55 g of p-toluenesulfonyl chloride (8.1 mmol) was added under ice-cooling,Stirring for 0.5 hours, removing the ice bath and reacting at room temperature for 3 hours;15 mL of deionized water was added, extracted, the organic phase was collected, the organic phase was washed with brine (50 g / L)Add 100mg anhydrous sodium sulfate drying, filtration, rotary evaporation to remove the organic solvent,The resulting solid was purified by silica gel chromatography (eluent: dichloromethane / methanol, V / V = 9: 1) to give solid 1,2-bis (2-toluenesulfonylethoxy) ethane(Yield 90.1percent).
88%
Stage #1: With potassium hydroxide In dichloromethane at 0 - 20℃;
Stage #2: at 20℃; for 10 h;
General procedure: KOH (20 g, 356.5 mmol for 9; and 10 g, 181.5 mmol for 10–11) was added to 300 mL of a CH2Cl2 solution containing the oligoethylene glycol (10 g,94 mmol for 9, 66.6 mmol for 10, and 51.5 mmol for 11) at 0 °C. After stirring for 30 min at room temperature, TsCl (45 g, 236 mmol for 9–11) was added and the resulting solution was stirred for 10 h at room temperature. The resulting solution was filtered and then washed with aq. K2CO3. The organic layer was dried with MgSO4, filtered, and concentrated in vacuo. The resulting residue was then subjected to silicagel column chromatography (EtOAc:Hex = 1:1) to yield 35 g of 9 (90percent), 27 g of 10 (88percent), and 23 g of 11 (89percent).
87% With triethylamine In dichloromethane at 20℃; for 12 h; To a solution of 14 (4.5 g, 30.0 mmol) and TsCl (12.59 g, 66.0 mmol) in DCM (100 mL) was added NEt3 (6.68 g, 66.0 mmol). The reaction mixture was stirred at rt for 12 h and washed with water. The organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was purified by flash column chromatography (0-40percent EtOAc/hexanes) to afford 15 as a white solid (12.0 g, 87percent). 1H NMR (CDCl3, 600 MHz) δ 7.78 (d, J = 7.8 Hz, 4H), 7.34 (d, J = 7.8 Hz, 4H), 4.19-4.10 (m, 4H), 3.70-3.62 (m, 4H), 3.57-3.48 (m, 4H), 2.44 (s, 6H). HRMS (ESI+) calcd for C20H26NaO8S2 (M+Na)+ 481.0961, found 481.0963.
87% With triethylamine In dichloromethane at 20℃; for 8 h; p-toluenesulfonyl chloride (40.63 g, 213.09 mmol) was dissolved in methylene chloride (MC, 150 mL) in a 500 mL 1 neck round flask and, then, triethyleneglycol (16 g, 105.55 mmol) and triethylamine (29.72 mL, 213.09 mmol) were added. The reacting mixture was stirred at room temperature for 8 hr. After reaction, 200 mL of distilled water was added and extraction was carried out by using 600 mL of chloroform (CHCl3). After removing the solvents, products were separated by column chromatography (silica, hexane/ethyl acetate=1:1 (v/v)). (yield=42.59 g, 87percent)1H NMR (400 MHz, CDCl3): δ 7.80-7.78 (d, 4H), 7.35-7.33 (d, 4H), 4.15-4.12 (t, 4H), 3.66-3.64 (t, 4H), 3.52 (s, 4H), 2.44 (s, 6H). (See, FIG. 9).
76% With triethylamine In tetrahydrofuran at 20℃; for 12 h; Inert atmosphere To a solution of triethylene glycol (6 g, 40.00 mmol) in THF (80 mL) was added Et3N (10.12 g, 100.00mmol). Tosyl chloride (15.6 g, 80.00 mmol) was added and stirred at room temperature for 12 h. Thesolvent was removed under reduced pressure and the residue was dissolved in EtOAc. The organic layerwas washed with aqueous 1N HCl and brine. The organic layer was dried over Na2SO4, and concentratedunder reduced pressure. The crude residue was purified by flash column chromatography (EtOAc: Hexane= 10: 1) to afford compound 19 as a clear colorless oil in 76 percent yield (14 g). This compound was alreadyreported.2 1H NMR (400 MHz, DMSO-d6) δ 7.81 (d, J = 8.2 Hz, 4H), 7.50 (d, J = 7.8 Hz, 4H), 4.13 (t, J =4.3 Hz, 4H), 3.57 (t, J = 4.3 Hz, 4H), 3.41 (s, 4H), 2.45 (s, 6H); 13C NMR (100 MHz, DMSO-d6) δ 144.89,132.38, 130.13, 127.63, 69.98, 69.82, 69.70, 69.65, 69.19, 67.86, 65.53, 21.09, 15.11. ESI-MS: m/z = 459(M + H)+.
64% With triethylamine In diethyl ether at 20℃; for 18 h; Inert atmosphere To a solution of triethylene glycol (3 g, 0.02 mol) in diethyl ether (40 mL), triethylamine (7.8 g, 0.04 mol) was added at room temperature, followed by addition of p-toluenesulfonyl chloride (7.8 g, 0.04 mol) under argon atmosphere. The mixture was stirred at room temperature for 18 h (TLC monitoring, ethyl acetate/hexanes, 1:4). The organic solvents were removed under reduced pressure. The residue was dissolved in methylene chloride (20 mL), washed with sodium bicarbonate (20 mL, saturated), water (20 mL .x. 2), brine (30 mL), dried over magnesium sulfate and concentrated under vacuum. Colorless crystals of triethylene glycol ditosylate were obtained from ethyl acetate.Yield = 5.8 g, 64percent mp: 75-77 °C. Rf = 0.5 (ethyl acetate/hexanes, 1:4). 1H NMR (300 MHz, CDCl3): δ 7.78 and 7.34 (AA'BB', 8H), 4.12 (d, 4H), 3.65 (t, 4H), 3.53 (s, 4H), 2.45 (s, 6H). 13C NMR (75 MHz, CDCl3, δ 145.1, 133.3, 130.1, 128.2, 70.9, 69.4, 69.0, 21.8.
13.74 g With sodium hydroxide In tetrahydrofuran; water 5 g (33.3 mmol) of triethylene glycol and 13.96 g (73.2 mmol) of 4-toluenesulfonyl chloride were dissolved in tetrahydrofuran 100ml and stirred. Then, 4.66 g (116.5 mmol) of sodium hydroxide was dissolved in the minimum amount of water," After completion of the reaction, diethyl ether and water were added to separate the layers, and the mixture was concentrated under reduced pressure,To give 13.74 g (29.97 mmol) of the titled compound.

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[ 113826-06-5 ]

(2R)-(-)-Glycidyl tosylate

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Chemical Structure| 70987-78-9

[ 70987-78-9 ]

(s)-(+)-oxirane-2-methanol p-toluenesulfonate

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