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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Diethylene glycol bis(p-toluenesulfonate) is a reagent used for the preparation of crosslinked polymers, and can be used in conjugation and labeling applications.
Synonyms: Diethylene glycol di(p-toluenesulfonate); Bis-Tos-PEG2; Oxybis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate)
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 7460-82-4 |
Formula : | C18H22O7S2 |
M.W : | 414.49 |
SMILES Code : | O=S(C1=CC=C(C)C=C1)(OCCOCCOS(C2=CC=C(C)C=C2)(=O)=O)=O |
Synonyms : |
Diethylene glycol di(p-toluenesulfonate); Bis-Tos-PEG2; Oxybis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate)
|
MDL No. : | MFCD00026001 |
InChI Key : | VYVPNTJBGPQTFA-UHFFFAOYSA-N |
Pubchem ID : | 316659 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium iodide; In acetone; at 60℃; for 10h; | General procedure: NaI (5 g, 33.3mmol) was added to 150 mL of an acetone solution containing tosylate (5 g, 12.1 mmol (12), 10.9 mmol (13) and 9.9 mmol(14)), and the resulting solution was stirred at 60 C for 10 h. After filtering the remaining NaI, the resulting mixture was concentrated in vacuo. The residue was extracted with CH2Cl2. The extract was dried with MgSO4, filtered, and concentrated in vacuo to give 15 (3.6 g, 91%), 16 (3.7 g, 92%), and 17 (3.7 g, 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | Diethyleneglycol (1.25 g, 11.8 mmol) was dissolved in water (3.5 mL) and sodium hydroxide (0.768 g, 19.2 mmol) was added. The mixture was stirred at room temperature until a clear solution was obtained. The mixture was cooled to 0°C and a solution of 4-toluene sulfonylchloride (2.27 g, 1 1.9 mmol) in tetrahydrofuran (30 mL) was dropwise added over a period of 20 minutes. After the addition was completed, the reaction mixture was stirred at 0°C for 1 hour. The reaction mixture was diluted with ethyl acetate (150 mL) and water (40 mL). The organic phase was separated, dried over Na2S04, filtered and the solvents were evaporated under reduced pressure. The residue was purified on HP-Sil SNAP cartridges using a Biotage Isolera One purification system employing an dichloromethane/methanol gradient (100/0 ->100/0) to afford the more polar title compound as a colorless oil (1.47 g, 47 percent). The less polar bis-tosyl derivative was discarded. 1H-NMR (400 MHz, CDCI3) delta = 7.80 (d, 2H), 7.35 (d, 2H), 4.22-4.18 (m, 2H), 3.72-3.66 (m, 4H), 3.55-3.51 (m, 2H), 2.45 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | To a stirred solution of propargyl alcohol (100 mg, 1.8 mmol) in dry DMF (30 mL) was added NaH (60% in oil, 900 mg, 22 mmol) at 0 C under Ar. After stirring for 30 min at room temperature, diethylene glycol bis(p-toluenesulfonate) (2.8 g, 6.7 mmol) was added to the mixture at 0 C. The mixture was stirred for 1 h at room temperature. After quenching with sat. NH4Cl at 0 C, the resulting mixture was extracted with EtOAc (250 mL × 3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residual oil was purified by silica gel column chromatography with 20% EtOAc in hexane to obtain 1 (410 mg, 78%) as a colorless oil. 1H NMR (270 MHz, CDCl3): δ 2.43 (1H, t, J = 2.6 Hz, H-1), 2.45 (3H, s, CH3 in tosylate), 3.59-3.66 (4H, m, -OCH2CH2O-), 3.70 (2H, m, -OCH2CH2OSO2-), 4.16 (2H, m, HCCCH2O-), 4.17 (2H, m, -OCH2CH2OSO2-), 7.34 and 7.80 (each 2H, m, tosylate); HRMS (ESI-TOF, positive mode): calcd for C14H18O5SNa [M+Na]+ 321.0773, found 321.0771. | |
60% | 250 μL (4.23 mmol) of propargyl alcohol was dissolved in 30 mL of dehydrated dimethylformamide, and 348 mg (8.7 mmol) of 60% sodium hydride was added thereto and stirred at room temperature for 30 minutes. 3.5 g (8.5 mmol) of diethylene glycol bis(p-toluene sulfonate) was added thereto while cooling with ice, thereby starting the reaction. After stirring at room temperature for 1 hour, 15 mL of a saturated aqueous solution of ammonium chloride was added thereto thereby terminating the reaction. 60 mL of water was added thereto, 3 mL of 1M hydrochloric acid was added thereto to adjust pH to be 7, and subsequently the resultant was extracted three times with 100 mL of ethyl acetate. The resultant was washed twice with 3 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and subsequently concentrated under reduced pressure thereby obtaining 3262.5 mg of a mixture of a white solid and a light yellow oily substance. The mixture was subjected to silica gel column chromatography (150 g, 3.0 cm inner diameter×35 cm length) using hexane-ethyl acetate (75:25) as an eluent thereby obtaining 753.0 mg (2.523 mmol; yield 60%) of the titled compound as a colorless clear oily substance. |
Tags: Diethylene glycol bis(p-toluenesulfonate) | Diethylene glycol di(p-toluenesulfonate) | Sulfonates | Aryls | Ethers | Sulfonic Acids | PEG Linkers | Organic Building Blocks | Bifunctional Linkers | PROTAC Linkers | 7460-82-4
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H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
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H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
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H318 | Causes serious eye damage |
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H362 | May cause harm to breast-fed children |
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H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
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H401 | Toxic to aquatic life |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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