THP-PEG2-alcohol

 CAS No.: 2163-11-3  Cat No.: BP-500897  Purity: ≥95% 4.5  

THP-PEG2-alcohol is a polyethylene glycol (PEG)-based linker alcohol featuring a short, two–ethylene glycol unit chain that provides a flexible, hydrophilic spacer between a THP-derived recognition element and a terminal functional group suitable for further conjugation. Structurally, it combines PEG-mediated solvation and conformational mobility with an alcohol handle that can be used to enable coupling strategies commonly employed in PROTAC synthesis, such as conversion to activated derivatives for attachment to warheads or E3-ligase–binding moieties. In targeted protein degradation designs, this type of linker helps tune the effective distance and relative orientation required for productive ternary complex formation, often improving the probability of simultaneous engagement of the target protein and the recruited E3 ligase while reducing nonproductive hydrophobic contacts. As a compact PEG spacer, it is particularly useful for optimizing degraders where minimal linker length is desired, supporting systematic structure–activity relationship studies in PROTAC development.

THP-PEG2-alcohol

Structure of 2163-11-3

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Category
PROTAC Linker
Molecular Formula
C9H18O4
Molecular Weight
190.24
Related CAS
92417-25-9 (polymer) 301295-36-3 (polymer)
Appearance
Clear Colorless Oily Matter

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

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Purity
≥95%
Solubility
Soluble in Chloroform (Slightly), Methanol (Slightly)
Appearance
Clear Colorless Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-(oxan-2-yloxy)ethoxy]ethanol
Synonyms
OH-PEG2-THP; THP-PEG3; HO-PEG2-THP; THP-PEG2-OH; Tetrahydropyranyldiethyleneglycol; 2-[2-(Tetrahydropyranyloxy)ethoxy]ethanol; Diethylene Glycol Mono(tetrahydro-2-pyranyl) Ether; Ethanol, 2-[2-[(tetrahydro-2H-pyran-2-yl)oxy]ethoxy]-; 2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethan-1-ol; 2-[2-(Tetrahydro-2H-pyran-2-yloxy)ethoxy]ethanol; 2-[2-(oxan-2-yloxy)ethoxy]ethan-1-ol
Boiling Point
310.3±37.0 °C at 760 mmHg
Density
1.08±0.1 g/cm3
InChI Key
CPCUDERUJBARLD-UHFFFAOYSA-N
InChI
InChI=1S/C9H18O4/c10-4-6-11-7-8-13-9-3-1-2-5-12-9/h9-10H,1-8H2
SMILES
C1CCOC(C1)OCCOCCO

THP-PEG2-alcohol is a polyethylene glycol (PEG)-based linker building block designed to support the modular synthesis of PROTACs by providing a flexible hydrophilic spacer for connecting targeting and E3-ligand moieties. Its ether-rich backbone and terminal alcohol functionality make it compatible with common linker-installation strategies, helping to tune solubility, conformational freedom, and effective spatial presentation of ligands. The points below describe the structure and practical reactivity considerations for PROTAC assembly in detail.

Structure: THP-PEG2-alcohol comprises a tetrahydropyran (THP) protected motif linked to a short PEG chain, featuring multiple ether linkages and a terminal primary alcohol. The scaffold contains stable C–O and C–C bonds, with conformational flexibility typical of PEG spacers that enhance aqueous compatibility.

Reactivity: The terminal alcohol enables coupling or functional-group interconversion under standard organic synthesis conditions used for PROTAC linker construction, including formation of activated derivatives for subsequent nucleophilic substitution. The THP group can be selectively removed under mild acidic conditions to reveal the corresponding alcohol for further conjugation. Typical workflows employ dry polar aprotic solvents, acid/base-neutral conditions for stability, and established coupling reagents compatible with PEG ethers.

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It is commonly abbreviated as: C1V1 = C2V2

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Historical Records: mPEG3-CH2CH2COONHS ester | Mal-PEG6-NHS | HO-PEG16-OH | DBCO-C-PEG1 | DNP-PEG4-NHS ester | DBCO-PEG1-NHS ester | Thalidomide-5-(C6-amine) | m-PEG3-S-PEG3-Boc | Thalidomide-5-(PEG2-amine) | Allyl-PEG4-OH | THP-PEG2-alcohol

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