1-Phenyl-2,5,8,11-tetraoxatridecan-13-yl methanesulfonate Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

form 

Viscous Liquid

color 

Light yellow to yellow

1-Phenyl-2,5,8,11-tetraoxatridecan-13-yl methanesulfonate Usage And Synthesis

Uses

Benzyl-PEG4-MS is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs[1].

Synthesis

1. To a stirred mixture of 1-phenyl-2,5,8,11-tetraoxatridecan-13-ol (45.1 g, 159 mmol) and triethylamine (62.2 g, 636 mmol) in dichloromethane (800 mL) at 0 °C was slowly added methanesulfonyl chloride (36.4 g, 318 mmol). 2. After addition, the reaction mixture was stirred at room temperature overnight. 3. Upon completion of the reaction, the reaction was quenched with 1N HCl (300 mL) and then extracted with ethyl acetate. 4. The organic phases were combined, dried over magnesium sulfate, concentrated to dryness, and purified by fast chromatography to afford 1-benzyloxytrioxaundecanemethanesulfonate (56.2 g, 98%) as a clear oil. 1H NMR (400MHz, CDCl3) δ 7.25-7.32 (m, 5H), 4.54 (s, 2H), 4.32-4.34 (m, 2H), 3.71-3.73 (m, 2H), 3.59-3.66 (m, 12H), 3.03 (s, 3H).

IC 50

PEGs

References

[1] An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562 DOI:10.1016/j.ebiom.2018.09.005

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