581065-94-3

Basic information

• Product Name: Tos-PEG5 t-butyl ester
• Synonyms: Tos-PEG5 t-butyl ester;tert-Butyl 1-(Tosyloxy)-3,6,9,12-tetraoxapentadecan-15-oate
• CAS NO: 581065-94-3
• Molecular Formula: C₂₂H₃₆O₉S
• Molecular Weight: 476.58084
• Mol File: 581065-94-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 560.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.151±0.06 g/cm3(Predicted)
• Refractive Index: 1.49
• CAS DataBase Reference: Tos-PEG5 t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Tos-PEG5 t-butyl ester(581065-94-3)
• EPA Substance Registry System: Tos-PEG5 t-butyl ester(581065-94-3)

Safety Data

• Hazardous Substances Data: 581065-94-3(Hazardous Substances Data)

Usage

Description

Tos-PEG5 t-butyl ester is a PEG (polyethylene glycol) linker that features a t-butyl ester and a tosyl group. This molecule is characterized by its hydrophilic PEG spacer, which enhances solubility in aqueous media, and a t-butyl protected carboxyl group that can be deprotected under acidic conditions. The tosyl group serves as an excellent leaving group for nucleophilic substitution reactions, making Tos-PEG5 t-butyl ester a versatile compound in various applications.

Uses

Used in Pharmaceutical Industry:
Tos-PEG5 t-butyl ester is used as a PEGylation agent for improving the solubility and bioavailability of drugs. The hydrophilic PEG spacer increases the water solubility of the drug, while the t-butyl ester and tosyl group facilitate chemical modifications and conjugations, enhancing the drug's overall performance in the body.
Used in the Preparation of Taxanes:
Tos-PEG5 t-butyl ester is used as a key component in the synthesis of taxanes, a class of chemotherapy drugs. Tos-PEG5 t-butyl ester contributes to the improved toxicity and solubility of taxanes in aqueous solutions compared to traditional paclitaxel, making it a valuable asset in the development of more effective cancer treatments.

Upstream product

• 133-59-5 Toluene-2-sulfonyl chloride 
• 518044-32-1 tert-butyl 3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)propanoate 
• 4792-15-8 Pentaethylene glycol 
• 1663-39-4 tert-Butyl acrylate 
• 112-60-7 Tetraethylene glycol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 581065-95-4 tert-butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate 
• 581066-04-8 tert-butyl 1-azido-3,6,9,12-tetraoxapentadecan-15-oate 
• 1415329-56-4 C₂HF₃O₂*C₅₅H₉₆N₆O₁₃ 
• 1415329-57-5 C₅₁H₈₈N₆O₁₃*ClH 
• 663921-15-1 3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid 
• 1415328-95-8 Phth-PEG₄-OSu 
• 1393330-38-5 C₁₁H₂₁BrO₆ 
• 778596-20-6 34-(p-toluenesulfonyl)-4,7,10,13,16,19,22,25,28,31,34-undecaoxatetracontanoic acid tert-butyl ester 
• 778596-28-4 3-(2-{2-[2-(2-{2-[2-(2-{2-[2-(2-mercapto-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid tert-butyl ester 
• 778596-26-2 tert-butyl 1-hydroxy-3,6,9,12,15,18,21,24,27,30-decaoxatritriacontan-33-oate 
• 564476-33-1 15-mercapto-4,7,10,13-tetraoxapentadecanoic acid tert-butyl ester 
• 778596-25-1 3-(2-{2-[2-(2-{2-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid tert-butyl ester 

Relevant articles and documents

Design, Synthesis, and Evaluation of WD-Repeat-Containing Protein 5 (WDR5) Degraders

Histone H3K4 methylation serves as a post-translational hallmark of actively transcribed genes and is introduced by histone methyltransferase (HMT) and its regulatory scaffolding proteins. One of these is the WD-repeat-containing protein 5 (WDR5) that has also been associated with controlling long noncoding RNAs and transcription factors including MYC. The wide influence of dysfunctional HMT complexes and the typically upregulated MYC levels in diverse tumor types suggested WDR5 as an attractive drug target. Indeed, protein-protein interface inhibitors for two protein interaction interfaces on WDR5 have been developed. While such compounds only inhibit a subset of WDR5 interactions, chemically induced proteasomal degradation of WDR5 might represent an elegant way to target all oncogenic functions. This study presents the design, synthesis, and evaluation of two diverse WDR5 degrader series based on two WIN site binding scaffolds and shows that linker nature and length strongly influence degradation efficacy.

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.

Preparation method, raw material, product and application of photo-crosslinking hydrogel material

The invention provides a preparation method, a raw material, a product and an application of a photo-crosslinking hydrogel material. The preparation method comprises the steps of dissolving a component A, namely a photosensitive high polymer derivative, i