882518-89-0

Basic information

• Product Name: Tos-PEG3-CH2CO2tBu
• Synonyms: Tos-PEG3-CH2CO2tBu;Tos-PEG2-CH2COOtBu;tert-butyl 2-(2-(2-(tosyloxy)ethoxy)ethoxy)acetate
• CAS NO: 882518-89-0
• Molecular Formula: C₁₇H₂₆O₇S
• Molecular Weight: 374.44914
• Mol File: 882518-89-0.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• Solubility: Soluble in DMSO, DCM, DMF
• CAS DataBase Reference: Tos-PEG3-CH2CO2tBu(CAS DataBase Reference)
• NIST Chemistry Reference: Tos-PEG3-CH2CO2tBu(882518-89-0)
• EPA Substance Registry System: Tos-PEG3-CH2CO2tBu(882518-89-0)

Safety Data

• Hazardous Substances Data: 882518-89-0(Hazardous Substances Data)

Usage

Description

Tos-PEG3-CH2CO2tBu is a PEG (polyethylene glycol) linker that features a t-butyl ester and a tosyl group. This molecule is designed to enhance solubility in aqueous environments due to the hydrophilic nature of the PEG spacer. Additionally, the t-butyl protected carboxyl group allows for deprotection under acidic conditions, and the tosyl group serves as an excellent leaving group for nucleophilic substitution reactions, making Tos-PEG3-CH2CO2tBu a versatile component in various chemical and pharmaceutical applications.

Uses

Used in Bioconjugation and Drug Delivery:
Tos-PEG3-CH2CO2tBu is used as a bioconjugation agent for attaching biologically active molecules to other molecules or surfaces. The reason for its use in this application is the presence of a reactive tosyl group that facilitates nucleophilic substitution reactions, allowing for the formation of stable conjugates.
Used in the Synthesis of Prodrugs:
In the pharmaceutical industry, Tos-PEG3-CH2CO2tBu is used as a prodrug modifier. The t-butyl ester can be selectively removed under acidic conditions, such as those found in certain compartments of the body or in response to specific enzymes, to release the active drug. This property is utilized to improve the pharmacokinetics and biodistribution of drugs, as well as to reduce side effects by enabling targeted drug release.
Used in the Development of Smart Materials:
Tos-PEG3-CH2CO2tBu is employed as a component in the development of smart materials, such as stimuli-responsive hydrogels and drug delivery systems. The ability to deprotect the carboxyl group under specific conditions allows for the design of materials that can change properties or release payloads in response to environmental triggers, such as pH changes or enzymatic activity.
Used in Chemical Synthesis:
In the field of organic chemistry, Tos-PEG3-CH2CO2tBu is used as an intermediate in the synthesis of various complex molecules. The PEG spacer can be used to increase the solubility of intermediates and final products, while the tosyl group can be employed as a leaving group in subsequent reaction steps, facilitating the formation of desired products.

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 118591-58-5 5-tosyloxy-3-oxapentanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 149299-82-1 tert-butyl 2-(2-(2-hydroxyethoxy)ethoxy)acetate 

Downstream Products

• 251564-45-1 tert-butyl 2-(2-(2-azidoethoxy)ethoxy)acetate 

Relevant articles and documents

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Epidermal growth factor receptor (EGFR) is one of the important and valuable drug targets. Overexpression of EGFR is associated with the development of many types of cancer. In this study, three PROTACs small molecules (16a–16c) were designed, synthesized and evaluated for their cytotoxicity against the growth in different NSCLC cell line and the degradation effect. The bioassay results indicated that 16c has a good inhibition in PC9 cells and H1975 cells, and the corresponding IC50 value was 0.413 μM and 0.657 μM, respectively. Western blotting results demonstrated that compound 16c could serve as an effective EGFRdel19-targeting degrader in PC9 cells.