1309451-06-6

Basic information

• Product Name: 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester
• Synonyms: 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester
• CAS NO: 1309451-06-6
• Molecular Weight: 266.337
• Mol File: 1309451-06-6.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester(1309451-06-6)
• EPA Substance Registry System: 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester(1309451-06-6)

Safety Data

• Hazardous Substances Data: 1309451-06-6(Hazardous Substances Data)

Usage

Description

2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester, also known as Benzyl-PEG2-CH2CO2tBu, is a PEG linker containing a benzyl group and a t-butyl protected carbonyl. Both the benzyl and t-Butyl group can be removed under acidic conditions, and the carboxylic acid can be reacted with primary amines in the presence of activators such as EDC and DCC to form stable amide bonds. The hydrophilic PEG linkers increase the water solubility of the compound in aqueous media.
Used in Pharmaceutical Industry:
2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester is used as a protecting group for carboxylic acids in the synthesis of pharmaceutical compounds. The t-butyl group can be removed under acidic conditions, allowing for the formation of stable amide bonds with primary amines, which is essential for the synthesis of various drug molecules.
Used in Bioconjugation:
2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester is used as a bioconjugation agent for attaching biologically active molecules to other molecules or surfaces. The PEG linker provides increased water solubility and stability, while the benzyl and t-butyl groups can be selectively removed under acidic conditions to reveal the carboxylic acid for subsequent reactions.
Used in Drug Delivery Systems:
2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester is used as a component in drug delivery systems to improve the solubility and stability of drug molecules. The PEG linker can enhance the water solubility of hydrophobic drugs, while the benzyl and t-butyl groups can be removed under acidic conditions to release the active drug molecule in a controlled manner.

Upstream product

• 100-39-0 benzyl bromide 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 622-08-2 2-Benzyloxyethanol 

Downstream Products

• 93206-09-8 <2-(benzyloxy)ethoxy>acetic acid 
• 287174-32-7 (2-hydroxyethoxy)acetic acid tert-butyl ester 
• 1155811-37-2 tert-butyl 2-(2-aminoethoxy)acetate 
• 1820717-35-8 2-azidoethoxyacetic acid tert-butyl ester 
• 1643957-24-7 tert-butyl 2-(2-[[(4-methylbenzene)sulfonyl]oxy]ethoxy)acetate 

Relevant articles and documents

Design, Synthesis, and Evaluation of VHL-Based EZH2 Degraders to Enhance Therapeutic Activity against Lymphoma

Traditional EZH2 inhibitors are developed to suppress the enzymatic methylation activity, and they may have therapeutic limitations due to the nonenzymatic functions of EZH2 in cancer development. Here, we report proteolysis-target chimera (PROTAC)-based EZH2 degraders to target the whole EZH2 in lymphoma. Two series of EZH2 degraders were designed and synthesized to hijack E3 ligase systems containing either von Hippel-Lindau (VHL) or cereblon (CRBN), and some VHL-based compounds were able to mediate EZH2 degradation. Two best degraders, YM181 and YM281, induced robust cell viability inhibition in diffuse large B-cell lymphoma (DLBCL) and other subtypes of lymphomas, outperforming a clinically used EZH2 inhibitor EPZ6438 (tazemetostat) that was only effective against DLBCL. The EZH2 degraders displayed promising antitumor activities in lymphoma xenografts and patient-derived primary lymphoma cells. Our study demonstrates that EZH2 degraders have better therapeutic activity than EZH2 inhibitors, which may provide a potential anticancer strategy to treat lymphoma.

POLYCYCLIC COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF RAPIDLY ACCELERATED FIBROSARCOMA POLYPEPTIDES

The present disclosure relates to bifunctional compounds, ULM— L—PTM, which find utility as modulators of Rapidly Accelerated Fibrosarcoma (RAF, such as c-RAF, A- RAF and/or B-RAF; the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein RAF, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein, or the constitutive activation of the target protein, are treated or prevented with compounds and compositions of the present disclosure.

Identification of New Small-Molecule Inducers of Estrogen-related Receptor α (ERRα) Degradation

A series of (E)-3-(4-((2,4-bis(trifluoromethyl)benzyl)oxy)-3-methoxyphenyl)-2-cyanoacrylamide derivatives were designed and synthesized as new estrogen-related receptor α (ERRα) degraders based on the proteolysis targeting chimera (PROTAC) concept. One of the representative compounds 6c is capable of specifically degrading ERRα protein by >80% at a relatively low concentration of 30 nM, becoming one of the most potent and selective ERRα degraders to date. Compound 6c could be utilized as a new powerful research tool for further biological investigation of ERRα.