1-(9-MERCAPTONONYL)-3,6,9-TRIOXAUNDECAN-11-OL

 CAS No.: 130727-41-2  Cat No.: BP-501354  Purity: 95% 4.5  

1-(9-MERCAPTONONYL)-3,6,9-TRIOXAUNDECAN-11-OL is a heteroatom-rich PROTAC linker featuring a triethylene glycol–like “trioxaundecane” scaffold that provides aqueous compatibility and conformational flexibility, terminating in a primary alcohol and an alkyl thiol-bearing side chain. The ether-rich backbone can reduce nonspecific hydrophobic interactions while allowing productive spatial positioning between the ligand-binding modules of a PROTAC. The terminal thiol functionality is particularly useful for chemoselective conjugation strategies, including formation of thioether or disulfide linkages to electrophilic handles introduced on E3 ligase ligands or other targeting moieties. In targeted protein degradation research, such linkers help tune linker length, polarity, and effective reach, thereby influencing ternary complex formation and degradation potency. This compound is therefore valuable for systematic PROTAC optimization workflows where linker architecture and attachment chemistry are key experimental variables.

1-(9-MERCAPTONONYL)-3,6,9-TRIOXAUNDECAN-11-OL

Structure of 130727-41-2

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Category
PROTAC Linker
Molecular Formula
C17H36O4S
Molecular Weight
336.53
Appearance
Colourless Oil

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

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Purity
95%
Appearance
Colourless Oil
Application
Long chain alkanethiol suitable for self-assembly from solution onto gold surfaces. The control of surface functionality using these self-assembled monolayers (SAMs) makes the exploration of such interactions as protein recognition possible.
Storage
-20 °C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-(11-sulfanylundecoxy)ethoxy]ethoxy]ethanol
Synonyms
TRI(ETHYLENE GLYCOL) MONO-11-MERCAPTOUN&; 11-Mercaptoundecanoltriethyleneglycolether
Boiling Point
446.5°C at 760 mmHg
Density
0.995 g/mL at 25 °C
InChI Key
FASSFROSROBIBE-UHFFFAOYSA-N
InChI
InChI=1S/C17H36O4S/c18-10-12-20-14-16-21-15-13-19-11-8-6-4-2-1-3-5-7-9-17-22/h18,22H,1-17H2
SMILES
C(CCCCCOCCOCCOCCO)CCCCCS

1-(9-Mercaptononyl)-3,6,9-trioxaundecan-11-ol, is designed to provide a flexible, hydrophilic spacer that can be positioned to connect ligands while supporting effective ternary-complex formation. Its ether-rich backbone and terminal functional handle enable modular synthesis of targeted protein degraders. The subsequent sections describe its structural features and practical considerations for assembling PROTAC architectures using this linker.

Structure: The linker contains a tri-ether (oxane/ether) segment that imparts conformational flexibility and polarity, together with a terminal aliphatic alcohol and a thio-functional group suitable for chemoselective coupling. It is composed of saturated carbon–heteroatom frameworks with stable C–O and C–S connectivity.

Reactivity: The terminal alcohol can be converted to activated electrophiles (for example, via standard esterification or leaving-group formation) under mild conditions, enabling coupling to nucleophilic partners used in PROTAC synthesis. The thiol functionality is amenable to selective derivatization through thiol–electrophile reactions or disulfide-based strategies, often requiring controlled pH and inert atmosphere to minimize oxidation. Typical solvents include polar aprotic media, with coupling steps guided by established amide/ester/thiol-conjugation protocols.

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Historical Records: Thalidomide-4-NH-PEG1-NH-Boc | SJF620 | 3-Methyl-L-valyl-(4R)-4-hydroxy-N-{(1R)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl}-L-prolinamide | Pomalidomide 4'-PEG3-azide | Thalidomide-4-O-CH2-COO(t-Bu) | Thalidomide-NH-CH2-COO(t-Bu) | Thalidomide-5-O-CH2-COO(t-Bu) | Pomalidomide-C3-NH2 hydrochloride | 3-(4-methoxy-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione | m-PEG2-O-Ph-NH2 | 1-(9-MERCAPTONONYL)-3,6,9-TRIOXAUNDECAN-11-OL

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