| Identification | Back Directory | [Name]
m-PEG5-Tos | [CAS]
62921-76-0 | [Synonyms]
m-PEG5-OTs
m-PEG5-Tos
MPEG5-TOSYLATE
(CH3(OCH2CH2)4OTs)
TosO-(CH2CH2O)4-Me
2,5,8,11-tetraoxatridecan-13-ol tosylate
2,5,8,11-Tetraoxatridecan-13-ol, 4-methylbenzenesulfonate
3,6,9,12-Tetraoxatridecan-1-ol, 1-(4-methylbenzenesulfonate) | [Molecular Formula]
C16H26O7S | [MDL Number]
MFCD11041134 | [MOL File]
62921-76-0.mol | [Molecular Weight]
362.44 |
| Chemical Properties | Back Directory | [Boiling point ]
468.3±40.0 °C(Predicted) | [density ]
1.164±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Liquid | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Description]
m-PEG5-Tos is a PEG linker containing a tosyl group. The tosyl group is a very good leaving group for nucleophilic substitution reactions. The hydrophilic PEG spacer increases solubility in aqueous media. | [Uses]
m-PEG4-Tos is a derivative of silybin ethers, extracted from patent CN105037337A (compound III-b). m-PEG4-Tos is a PEG-based PROTAC linker can be used in the synthesis of Silymarin (HY-W043277)[1]. | [Synthesis]
1. tetraethylene glycol monomethyl ether (2,5,8,11-tetraoxatridecan-13-ol, 5.0 g, 24.01 mmol) was dissolved in tetrahydrofuran (THF, 20.01 mL).
2. To the above solution, pyridine (5.83 mL, 72.0 mmol) and p-toluenesulfonyl chloride (4-methylbenzene-1-sulfonyl chloride, 5.49 g, 28.8 mmol) were added sequentially.
3. The reaction mixture was stirred at room temperature overnight.
4. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporator.
5. The concentrated residue was dissolved in dichloromethane. 6.
6. The organic phase was washed twice with saturated aqueous sodium bicarbonate. 7.
7. Combine the aqueous phases and back-extract with methylene chloride. 8.
8. All organic phases were combined and washed twice with 1N hydrochloric acid and once with saturated saline.
9. The organic phase was dried with anhydrous magnesium sulfate (MgSO?), filtered and concentrated to afford the target product 2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate (4.12 g, 11.37 mmol, 47.3% yield), which could be used for the subsequent reaction without further purification. | [IC 50]
PEGs | [References]
[1] Yuxia Zhao, et al. Derivative of silybin ethers, and synthetic method and application thereof. Patent CN105037337A. |
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