Boc-NH-PEG4-Ms

 CAS No.: 1447797-72-9  Cat No.: BP-501248  Purity: ≥95% 4.5  

Boc-NH-PEG4-Ms is a Boc-protected amino-terminated polyethylene glycol linker bearing a methanesulfonate (mesylate) leaving group, providing a chemically versatile bridge for PROTAC assembly. Structurally, it consists of a short PEG chain that imparts hydrophilicity and conformational flexibility, connected through a carbamate-protected nitrogen to a terminal mesylate handle suitable for nucleophilic substitution. In PROTAC design, the mesylate terminus acts as the electrophile and undergoes nucleophilic substitution with an amine, thiol, alkoxide, or other suitable nucleophile, while the PEG segment helps reduce steric constraints and can improve solubility and effective intramolecular positioning of the two binding events. As a modular building block, it supports systematic variation of linker chemistry to tune degradation potency and cooperativity, facilitating reproducible synthesis of targeted protein degraders for mechanistic and optimization studies.

Boc-NH-PEG4-Ms

Structure of 1447797-72-9

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Category
PROTAC Linker
Molecular Formula
C14H29NO8S
Molecular Weight
371.45
Appearance
Colorless Oily Matter

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

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Purity
≥95%
Solubility
Soluble in DCM
Appearance
Colorless Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethyl methanesulfonate
Synonyms
t-Boc-N-Amido-PEG4-Ms; 5,8,11,14-Tetraoxa-15-thia-2-azahexadecanoic acid, 1,1-dimethylethyl ester, 15,15-dioxide; 2,2-Dimethyl-4-oxo-3,8,11,14-tetraoxa-5-azahexadecan-16-yl methanesulfonate; Carbamic acid, N-[2-[2-[2-[2-[(methylsulfonyl)oxy]ethoxy]ethoxy]ethoxy]ethyl]-, 1,1-dimethylethyl ester; 2-[2-[2-[2-(tert-Butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethyl methanesulfonate
Boiling Point
510.9±45.0°C (Predicted)
Density
1.166±0.06 g/cm3 (Predicted)
InChI Key
ALCCXXPVRZCVPC-UHFFFAOYSA-N
InChI
InChI=1S/C14H29NO8S/c1-14(2,3)23-13(16)15-5-6-19-7-8-20-9-10-21-11-12-22-24(4,17)18/h5-12H2,1-4H3,(H,15,16)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOS(=O)(=O)C

Boc-NH-PEG4-Ms is a PEG-based, methanesulfonate-activated linker designed for efficient installation of amine-containing ligands in PROTAC architectures. Its PEG segment provides conformational flexibility and improved solubility, while the activated leaving group supports robust coupling under standard organic synthesis conditions. This product is well suited for assembling targeted protein degradation constructs, and the following sections describe its structure and practical reactivity considerations in detail.

Structure: The linker contains a Boc-protected amine connected to a polyethylene glycol chain, terminating in a methanesulfonate leaving group. It features ether linkages within the PEG backbone and carbamate functionality from the Boc group, with polar, hydrogen-bonding-capable motifs that enhance aqueous compatibility.

Reactivity: The methanesulfonate activation enables nucleophilic substitution by amines to form stable C–N bonds, typically via an SN2-type displacement. Coupling is commonly performed under anhydrous conditions in polar aprotic solvents, using base to promote nucleophile formation. Boc deprotection can be used when required to expose the amine for subsequent conjugation steps, following established protecting-group chemistry.

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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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