Heptaethylene glycol dimethanesulfonate

 CAS No.: 109789-41-5  Cat No.: BP-501136  Purity: ≥95% 4.5  

Heptaethylene glycol dimethanesulfonate is a bifunctional, PEG-based linker reagent featuring an extended heptaethylene glycol spacer terminated with two methanesulfonate leaving groups. The long, flexible poly(ethylene glycol) chain provides conformational spacing and hydrophilicity, while the methanesulfonate termini enable efficient nucleophilic substitution by amines or other nucleophiles commonly used to install PROTAC “handles” on ligands. In PROTAC design, this linker mediates the spatial and chemical connection between an E3 ligase-binding moiety and a target-binding ligand, promoting productive ternary complex formation by reducing steric clashes and improving aqueous solubility of the assembled degrader. Its PEG architecture is widely used in targeted protein degradation workflows to tune linker length and dynamics, supporting systematic structure–activity relationship studies. Overall, it is a practical building block for generating conjugates that require robust, modular coupling chemistry and improved solubility for experimental evaluation.

Heptaethylene glycol dimethanesulfonate

Structure of 109789-41-5

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Category
PROTAC Linker
Molecular Formula
C16H34O12S2
Molecular Weight
482.56

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

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Purity
≥95%
Solubility
Soluble in DCM, DMF, DMSO
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
2-[2-[2-[2-[2-[2-(2-methylsulfonyloxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl methanesulfonate
Synonyms
Ms-PEG8-Ms; Ms-PEG7-Ms; 3,6,9,12,15,18-Hexaoxaeicosane-1,20-diol, 1,20-dimethanesulfonate; 3,6,9,12,15,18-Hexaoxaicosane-1,20-diyl dimethanesulfonate
Boiling Point
614.3±55.0°C at 760 mmHg
Density
1.3±0.1 g/cm3
InChI Key
HGSUQRYIYRXWTQ-UHFFFAOYSA-N
InChI
InChI=1S/C16H34O12S2/c1-29(17,18)27-15-13-25-11-9-23-7-5-21-3-4-22-6-8-24-10-12-26-14-16-28-30(2,19)20/h3-16H2,1-2H3
SMILES
CS(=O)(=O)OCCOCCOCCOCCOCCOCCOCCOS(=O)(=O)C

Heptaethylene glycol dimethanesulfonate is a multifunctional PROTAC linker building block designed to connect ligands through ether-rich, flexible spacing that can support productive ternary complex formation. Its sulfonate termini enable efficient covalent conjugation under standard organic synthesis workflows, facilitating the preparation of degraders with tunable linker length and solvation behavior. The structure and reactivity considerations for constructing PROTACs with this linker are described in detail below.

Structure: The linker comprises a heptaethylene glycol backbone featuring repeating ether units, capped by two methanesulfonate leaving groups. It contains ether linkages and sulfonate ester functionalities, providing flexibility, polarity, and good solubility in common polar organic media. These attributes help maintain conformational adaptability in PROTAC architectures.

Reactivity: The methanesulfonate groups serve as activated leaving groups for nucleophilic substitution, enabling coupling to nucleophile-bearing ligand fragments (for example, amines or other suitable nucleophiles) to form stable ether or related linkage motifs. Typical conditions employ polar aprotic or mixed solvents, with base to promote nucleophile generation and controlled temperature to balance reactivity and minimize side reactions. No special catalysts are generally required beyond standard base-mediated substitution practices used for sulfonate ester 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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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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