89346-82-7

Basic information

• Product Name: Tosylate of Tetraethylene glycol monobenzyl ether
• Synonyms: Tosylate of Tetraethylene glycol monobenzyl ether;2,5,8,11-Tetraoxatridecan-13-ol, 1-phenyl-, 4-methylbenzenesulfonate;1-phenyl-2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate
• CAS NO: 89346-82-7
• Molecular Formula: C₂₂H₃₀O₇S
• Molecular Weight: 456.54968
• Mol File: 89346-82-7.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Tosylate of Tetraethylene glycol monobenzyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Tosylate of Tetraethylene glycol monobenzyl ether(89346-82-7)
• EPA Substance Registry System: Tosylate of Tetraethylene glycol monobenzyl ether(89346-82-7)

Safety Data

• Hazardous Substances Data: 89346-82-7(Hazardous Substances Data)

Usage

Uses

Benzyl-PEG4-Ots is a PEG-based PROTAC linker that can be used to synthesize PROTACs.

in vitro

PROTAC contains two distinct ligands linked by a linker; one is a ligand for the E3 ubiquitin ligase and the other is a ligand for the target protein. PROTAC utilizes the intracellular ubiquitin-proteasome system to selectively degrade target proteins.

Upstream product

• 86259-87-2 1-phenyl-2,5,8,11-tetraoxatridecan-13-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 112-60-7 Tetraethylene glycol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 4792-15-8 Pentaethylene glycol 

Downstream Products

• 129086-17-5 [2-(2-{2-[2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluoro-octyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxymethyl]-benzene 
• 129086-20-0 [2-(2-{2-[2-(2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-heptyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxymethyl]-benzene 
• 134881-75-7 1,4-bis<2-<2-<2-<2-(benzyloxy)ethoxy>ethoxy>ethoxy>ethoxy>benzene 
• 86770-76-5 2-(2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethoxy)ethanamine 
• 134881-77-9 1,4-bis[2-(2-(2-(2-toluene-p-sulfonylethoxy)ethoxy)ethoxy)ethoxy]benzene 
• 134881-64-4 1,4-bis<2-<2-<2-<2-(4-benzyloxyphenoxy)ethoxy>ethoxy>ethoxy>ethoxy>benzene 
• 1050202-41-9 octaethylene glycol benzyl trityl ether 
• 1144113-13-2 octaethylene glycol benzyl tert-butyl ether 
• 361543-06-8 C₄₀H₆₆O₁₄ 
• 17598-96-8 poly(ethylene glycol) 600 

Relevant articles and documents

Effects of 18F-fluorinated neopentyl glycol side-chain on the biological characteristics of stilbene amyloid-β PET ligands

Introduction: The 2,2-dihydroxymethyl-1-[18F]fluoropropane group, also called 18F-labelled neopentyl glycol side-chain, is a novel 18F-labelling group for positron emission tomography (PET) imaging agents. The aim of using this group is to develop simple purification with solid-phase extraction without high-performance liquid chromatography. However, the effects of the neopentyl 18F-labelling group on the characteristics of brain imaging agents are unknown. Here, we added this side-chain to compounds with an aminostilbene structure to evaluate their effects on the biological properties of aminostilbene as an amyloid-β (Aβ) radioligand. Methods: Biodistributions of four novel 18F-labelled stilbene compounds with different lengths of polyethylene glycol (PEG) linkers, called [18F]Cpd-0, -1, -2, and -4, (PEG = 0, 1, 2, and 4), and [18F]AV-1 in normal mice were evaluated. Metabolite analysis of [18F]Cpd-0 and -1 was performed with mouse plasma and brain. A competitive binding assay of [18F]AV-1 binding to Aβ1–42 fibrils was performed to determine the binding properties of the compounds. Results: [18F]Cpd-0, -1, and -2 demonstrated moderate initial brain uptake in mice (3.1–4.2% injected dose/g at 2 min post-injection) followed by fast clearance, and in vivo defluorination of these compounds was negligible. [18F]Cpd-4 exhibited low brain uptake and high bone uptake. Compared with [18F]Cpd-1, the percentage of [18F]Cpd-0 in mouse brain was high at 10 min post-injection. A competitive binding assay revealed partial interference effects by the neopentyl glycol side-chain on binding of stilbene compounds to Aβ1–42 fibrils. Conclusions: Aminostilbene compounds with two or fewer PEG linkers containing an 18F-labelled neopentyl glycol side-chain demonstrated preferable pharmacokinetic properties as a brain imaging radioligand in normal mice. These side-chains can be used as an alternative labelling group for imaging agents targeting the brain.

SMALL-MOLECULE INHIBITORS FOR THE Β-CATENIN/B-CELL LYMPHOMA 9 PROTEIN?PROTEIN INTERACTION

Disclosed are inhibitors for the β-catenin/B-cell lymphoma 9 interaction. The inhibitors are selective for β-catenin/B-cell lymphoma 9 over β-catenin/ E-cadherin PPI interaction. Methods of using the disclosed compounds to treat cancer are also disclosed.

Optimization of IEDDA bioorthogonal system: Efficient process to improve trans-cyclooctene/tetrazine interaction

The antibody pretargeting approach for radioimmunotherapy (RIT) using inverse electron demand Diels-Alder cycloaddition (IEDDA) constitutes an emerging theranostic approach for solid cancers. However, IEDDA pretargeting has not reached clinical trial. The major limitation of the IEDDA strategy depends largely on trans-cyclooctene (TCO) stability. Indeed, TCO may isomerize into the more stable but unreactive cis-cyclooctene (CCO), leading to a drastic decrease of IEDDA efficiency. We have thus developed both efficient and reproducible synthetic pathways and analytical follow up for (PEGylated) TCO derivatives, providing high TCO isomeric purity for antibody modification. We have set up an original process to limit the isomerization of TCO to CCO before the mAbs’ functionalization to allow high TCO/tetrazine cycloaddition.