Boc-NH-PEG4-C2-Boc

 CAS No.: 2138484-13-4  Cat No.: BP-500196  Purity: ≥95% 4.5  

Boc-NH-PEG4-C2-Boc is a doubly protected, heterobifunctional PEG linker. Structurally, it contains a PEG4 chain with an N-Boc-protected amine at one end and a propionic acid protected as a tert-butyl ester at the other. Acidic deprotection of the tert-butyl ester reveals a carboxylic acid for amide or ester coupling, whereas removal of the N-Boc group exposes a primary amine for reaction with activated acids, isocyanates, or other suitable electrophiles. In PROTAC and related targeted protein degradation research, the two differentiated protecting groups support sequential attachment of a target-binding ligand and an E3 ligase–recruiting ligand without treating both termini as protected amines. Its defined architecture allows researchers to evaluate how linker polarity, flexibility, attachment sequence, and terminal-group selection influence conjugate preparation and the spatial requirements of productive target–E3 ligase engagement.

Boc-NH-PEG4-C2-Boc

Structure of 2138484-13-4

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Category
PROTAC Linker
Molecular Formula
C20H39NO8
Molecular Weight
421.53
Appearance
Colorless Oily Matter

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

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Purity
≥95%
Appearance
Colorless Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
N-Boc-PEG4-t-butyl ester; 5,8,11,14-Tetraoxa-2-azaheptadecanedioic acid, 1,17-bis(1,1-dimethylethyl) ester; 2-Methyl-2-propanyl 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oate; 3,8,11,14,17-Pentaoxa-5-azaeicosan-20-oic acid, 2,2-dimethyl-4-oxo-, 1,1-dimethylethyl ester
Boiling Point
497.2±40.0°C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
HOBFRUPMGLPRSJ-UHFFFAOYSA-N
InChI
InChI=1S/C20H39NO8/c1-19(2,3)28-17(22)7-9-24-11-13-26-15-16-27-14-12-25-10-8-21-18(23)29-20(4,5)6/h7-16H2,1-6H3,(H,21,23)
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCNC(=O)OC(C)(C)C

This Boc-protected PEG-based linker is designed for modular assembly of PROTACs, enabling reliable spacing and conformational flexibility between target-binding ligands. Its protected amine functionalities support controlled coupling strategies, helping researchers prepare degraders with reproducible architectures and minimized side reactions during synthesis. The details below describe its structural features and practical reactivity considerations for PROTAC construction.

Structure: The linker contains an oligo(ethylene glycol) segment providing hydrophilic, flexible spacing, flanked by Boc-protected amine termini. It features carbamate linkages from Boc groups and ether linkages within the PEG chain, yielding a polar, conformationally adaptable scaffold suitable for iterative amide or urea-forming chemistry.

Reactivity: Boc-protected amines are typically activated by acid-mediated deprotection to generate free amines, which then participate in standard PROTAC coupling reactions such as amide bond formation with activated carboxylic acids or acyl derivatives. Common approaches use coupling reagents and base in compatible organic solvents, while protecting-group stability should be maintained during ligand installation. Reaction design should follow established carbamate deprotection and amine-acylation principles to preserve linker integrity.

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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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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