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Azido-PEG4-Amido-tri-(t-butoxycarbonylethoxymethyl)-methane

Azido-PEG4-Amido-tri-(t-butoxycarbonylethoxymethyl)-methane

Name: Azido-PEG4-Amido-tri-(t-butoxycarbonylethoxymethyl)-methane
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1421933-29-0

Cat No.: BP-500663

Purity: ≥95% 4.5

Azido-PEG4-Amido-tri-(t-butoxycarbonylethoxymethyl)-methane is a functionalized, azide-bearing polyethylene glycol linker designed for modular PROTAC synthesis. Structurally, it comprises a short PEG4 spacer terminating in an azide handle and an amide-linked tri-substituted methane core bearing three orthogonally protected ethoxymethyl carbonate groups, which can be deprotected to reveal reactive sites for subsequent conjugation. In PROTAC architectures, the PEG spacer provides a flexible, hydrophilic distance element that can improve ternary complex formation by reducing steric clashes between the target-binding ligand and the E3 ligase ligand. The azide functionality enables copper-free or copper-catalyzed azide–alkyne cycloaddition (“click”) to install the linker onto complementary alkyne-bearing partners under mild conditions. This product is valuable for researchers who need precise, site-selective attachment chemistry and tunable linker geometry to systematically evaluate degradation efficiency and selectivity in targeted protein degradation studies.

Structure of 1421933-29-0

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Category

PROTAC Linker

Molecular Formula

C36H66N4O14

Molecular Weight

778.94

Appearance

Yellowish Oily Matter

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

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Purity

≥95%

Solubility

Soluble in DMSO

Appearance

Yellowish Oily Matter

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-[3-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]propanoylamino]-3-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propoxy]propanoate

Synonyms

tert-butyl 1-azido-17,17-bis((3-(tert-butoxy)-3-oxopropoxy)methyl)-15-oxo-3,6,9,12,19-pentaoxa-16-azadocosan-22-oate; 3-[2-[3-(2-(2-[2-(2-Azido-ethoxy)-ethoxy]-ethoxy)-ethoxy)-propionylamino]-3-(2-tert-butoxycarbonyl-ethoxy)-2-(2-tert-butoxycarbonyl-ethoxymethyl)-propoxy]-propionic acid tert-butyl ester; 2-Methyl-2-propanyl 1-azido-17,17-bis({3-[(2-methyl-2-propanyl)oxy]-3-oxopropoxy}methyl)-15-oxo-3,6,9,12,19-pentaoxa-16-azadocosan-22-oate; 3,6,9,12,19-Pentaoxa-16-azadocosan-22-oic acid, 1-azido-17,17-bis[[3-(1,1-dimethylethoxy)-3-oxopropoxy]methyl]-15-oxo-, 1,1-dimethylethyl ester; WUN 33290; WUN-33290; WUN33290

InChI Key

WXDPDERWOTZNLB-UHFFFAOYSA-N

InChI

InChI=1S/C36H66N4O14/c1-33(2,3)52-30(42)11-16-49-26-36(27-50-17-12-31(43)53-34(4,5)6,28-51-18-13-32(44)54-35(7,8)9)39-29(41)10-15-45-20-22-47-24-25-48-23-21-46-19-14-38-40-37/h10-28H2,1-9H3,(H,39,41)

SMILES

CC(C)(C)OC(=O)CCOCC(COCCC(=O)OC(C)(C)C)(COCCC(=O)OC(C)(C)C)NC(=O)CCOCCOCCOCCOCCN=[N+]=[N-]

This branched, multifunctional linker presents an azide for modular click attachment and several acid-labile ester termini for later diversification. Its oligoether-amide framework offers conformational reach and a central branching element suited to multivalent or exploratory PROTAC architectures. Detailed features appear below.

Structure: The molecule contains an azido-terminated oligoether segment connected through a stable amide to a tetrahedral branch center bearing ether-linked tert-butyl propanoates. Ether and carbon–carbon single bonds provide flexibility, while the amide adds polarity and local conformational constraint.

Reactivity: The terminal azide participates in cuprous-catalyzed cycloaddition with an alkyne in a water-compatible organic medium, typically using a copper-stabilizing ligand and reducing agent. Acid treatment removes the tert-butyl esters to furnish a polycarboxylic intermediate; its acids can then be activated for amide formation. Controlled stoichiometry and temporary protection are important to limit mixed substitution or intermolecular crosslinking.

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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