518044-32-1

Basic information

• Product Name: Hydroxy-PEG-5-t-butyl ester
• Synonyms: Hydroxy-PEG-5-t-butyl ester;PEG5-t-butly ester;Hydroxy-PEG4-t-butly ester;OH-PEG4-CH2CH2COOtBu
• CAS NO: 518044-32-1
• Molecular Formula: C₁₅H₃₀O₇
• Molecular Weight: 322.3945
• Mol File: 518044-32-1.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 406.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.04746 g/mL
• Refractive Index: n/D 1.4492
• Storage Temp.: 2-8°C
• Solubility: Soluble in Water, DCM
• PKA: 14.36±0.10(Predicted)
• CAS DataBase Reference: Hydroxy-PEG-5-t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxy-PEG-5-t-butyl ester(518044-32-1)
• EPA Substance Registry System: Hydroxy-PEG-5-t-butyl ester(518044-32-1)

Safety Data

• Hazardous Substances Data: 518044-32-1(Hazardous Substances Data)

Usage

Description

Hydroxy-PEG4-t-butyl ester is a PEG linker containing a hydroxyl group with a t-butyl ester. The hydrophilic PEG spacer increases solubility in aqueous media. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The t-butyl protected carboxyl group can be deprotected under acidic conditions.

Uses

This heterobifunctional, PEGylated crosslinker features a hydroxyl group at one end and t-butyl-protected carboxylic acid at the other, which can be deprotected with acidic conditions. The hydrophillic PEG linker facilitates solubility in biological applications. Hydroxy-PEG4-t-butyl ester can be used for bioconjugation or as a building block for synthesis of small molecules, conjugates of small molecules and/or biomolecules, or other tool compounds for chemical biology and medicinal chemistry that require ligation. Examples of applications include its synthetic incorporation into antibody-drug conjugates or proteolysis-targeting chimeras (PROTAC? molecules) for targeted protein degradation.

Upstream product

• 112-60-7 Tetraethylene glycol 
• 1663-39-4 tert-Butyl acrylate 
• 4792-15-8 Pentaethylene glycol 

Downstream Products

• 929087-90-1 3-[2-(2-{2-[2-(3-formyl-4-iodo-phenoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-propionic acid tert-butyl ester 
• 1291090-35-1 tert-butyl 1-(8-(4-(dimethylamino)phenyl)-1,2-dimethyl-7-oxopyrano[3,2-e]indol-3(7H)-yl)-3,6,9,12-tetraoxapentadecan-15-oate 
• 1291090-39-5 1-(8-(4-(dimethylamino)phenyl)-1,2-dimethyl-7-oxopyrano[3,2-e]indol-3(7H)-yl)-3,6,9,12-tetraoxapentadecan-15-oic acid 
• 1291090-26-0 N-[4-(2-amino-9H-purin-6-yloxymethyl)-benzyl]-3-{2-[2-(2-{2-[8-(4-dimethylamino-phenyl)-1,2-dimethyl-7-oxo-7H-pyrano[3,2-e]indol-3-yl]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionamide 
• 581065-94-3 tert-butyl 3-[2-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]ethoxy}ethoxy)ethoxy]propionate 
• 663921-15-1 3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid 
• 1393330-38-5 C₁₁H₂₁BrO₆ 
• 1427004-19-0 2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate 
• 870487-48-2 tert-butyl 1-(methanesulfonyloxy)-3,6,9,12-tetraoxapentadecan-15-oate 
• 1537170-85-6 1-(4-{2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid 
• 518044-41-2 1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,6,9,12-tetraoxapentadecan-15-oic acid 
• 518044-36-5 tert-butyl 15-maleimido-4,7,10,13-tetraoxapentadecanoate 

Relevant articles and documents

A new route for the synthesis of 1-amino-3,6,9,12-tetraoxapentadecan-15-oic acid

1-Amino-3,6,9,12-tetraoxapentadecan-15-oic acid 8 was synthesised from tetraethylene glycol through a 7 step sequence including esterification, mesylation, azide substitution with subsequent reduction followed by hydrolysis. The structure of product 8 was

USES OF ANTI-CD3 ANTIBODY FOLATE BIOCONJUGATES

Described herein are anti-CD3 antibody folate bioconjugates and uses thereof in the treatment of diseases, conditions, and cancers.

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.