Propargyl-PEG3-t-butyl ester

 CAS No.: 1374658-84-0  Cat No.: BP-500460  Purity: >95% 4.5  

Propargyl-PEG3-t-butyl ester is a heterobifunctional PEG-based linker featuring a terminal propargyl (alkyne) handle and a protected carboxylate masked as a tert-butyl ester. Structurally, it provides a short, flexible polyethylene glycol chain that increases solubility and spatial reach while maintaining chemical compatibility with common PROTAC assembly strategies. In targeted protein degradation workflows, the propargyl group enables chemoselective conjugation via click-type reactions to install the linker onto an E3 ligase ligand or a warhead-bearing scaffold, whereas the tert-butyl ester can be used to control reactivity during synthesis and then be converted to the free carboxylate for subsequent coupling steps. This combination of orthogonal functional groups and PEG-mediated flexibility makes the reagent valuable for constructing PROTACs with improved aqueous handling and tunable linker length, facilitating systematic structure–activity studies of ternary complex formation and degradation efficiency.

Propargyl-PEG3-t-butyl ester

Structure of 1374658-84-0

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Category
PROTAC Linker
Molecular Formula
C14H24O5
Molecular Weight
272.34
Appearance
Pale Yellow Oily Liquid

* For research and manufacturing use only. Not for human or clinical use.

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Purity
>95%
Solubility
Soluble in DMSO
Appearance
Pale Yellow Oily Liquid
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-(2-prop-2-ynoxyethoxy)ethoxy]propanoate
Synonyms
Propargyl-PEG3-COOtBu; Propargyl-PEG3-Boc; Alkyne-PEG3-CH2CH2COOtBu; Propargyl-PEG2-CH2COOtBu; tert-Butyl 3-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)propanoate; 2-Methyl-2-propanyl 3-{2-[2-(2-propyn-1-yloxy)ethoxy]ethoxy}propanoate; Propanoic acid, 3-[2-[2-(2-propyn-1-yloxy)ethoxy]ethoxy]-, 1,1-dimethylethyl ester; Propargyl-PEG3-t-Bu Ester
Boiling Point
337.2±27.0°C at 760 mmHg
Density
1.0±0.1 g/cm3
InChI Key
JCKIGUAOHLRKLH-UHFFFAOYSA-N
InChI
InChI=1S/C14H24O5/c1-5-7-16-9-11-18-12-10-17-8-6-13(15)19-14(2,3)4/h1H,6-12H2,2-4H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCC#C

Propargyl-PEG3-t-butyl ester is a PEG-based PROTAC linker building block designed to provide controlled spatial separation and solubility while retaining a functional handle for site-specific conjugation. The propargyl group enables reliable click-compatible coupling, and the t-butyl ester provides a chemically addressable protection motif that can be unmasked under appropriate conditions to reveal reactive carboxyl functionality. These features make the linker well suited for assembling targeted protein degraders, where linker geometry and reactivity strongly influence productive ternary complex formation. Detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a propargyl terminus attached to a polyethylene glycol segment and a terminal t-butyl ester. It contains an alkyne for bioorthogonal coupling, ether linkages within the PEG chain, and an ester linkage protected as a tert-butyl group, contributing to polarity and conformational flexibility.

Reactivity: The propargyl functionality is compatible with copper-catalyzed azide–alkyne cycloaddition or related alkyne-based coupling strategies commonly used in PROTAC synthesis. The t-butyl ester can be selectively cleaved to generate a carboxyl group for subsequent amide or ester bond formation. Typical preparation workflows use standard ester deprotection conditions and then proceed with coupling reactions under amide-forming conditions using appropriate bases and coupling reagents in compatible organic solvents, while minimizing alkyne degradation.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
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