2-(Tetrahydro-2H-pyran-2-yloxy)ethanol
CAS No.: 2162-31-4
Cat No.: BP-500230
Purity: ≥95%
4.5 
2-(Tetrahydro-2H-pyran-2-yloxy)ethanol is a protected, ether-linked diol building block featuring a tetrahydropyran (THP) acetal motif attached to a two-carbon hydroxymethyl chain. Structurally, it provides a stable oxygen linker that can be used to tune polarity, solubility, and synthetic handle availability in PROTAC construction. In targeted protein degradation designs, such linker fragments are commonly incorporated to spatially separate the ligand-binding warhead from the E3-recruiting element, thereby influencing productive ternary complex formation and the effective geometry required for ubiquitin transfer. The THP-protected hydroxyl functionality also supports stepwise assembly strategies, enabling controlled deprotection and subsequent coupling to other PROTAC modules. As a modular intermediate, it is valuable for researchers optimizing linker length, flexibility, and hydrogen-bonding capacity to improve degradation potency and selectivity in cellular assays.
Structure of 2162-31-4
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2-(Tetrahydro-2H-pyran-2-yloxy)ethanol, is designed to provide a chemically robust, ether-containing spacer that can be incorporated into targeted protein degradation constructs. Its acetal-derived tetrahydropyran motif and terminal hydroxymethyl functionality support modular synthesis of bifunctional degraders, enabling efficient coupling to warheads and ligands while maintaining conformational flexibility. The following sections describe the linker’s structure and practical reactivity considerations in PROTAC assembly.
Structure: The linker contains a tetrahydro-2H-pyran acetal ether connected to an ethyl chain bearing a primary alcohol. It features an ether linkage and a saturated cyclic acetal ring, with multiple heteroatoms that increase polarity and hydrogen-bonding capacity, supporting solubility and compatibility with common coupling chemistries.
Reactivity: The terminal primary alcohol enables standard PROTAC linker functionalization via activation to alkyl electrophiles or conversion to leaving groups for nucleophilic substitution. Typical approaches include esterification or etherification to form stable intermediates, followed by coupling to ligand-derived nucleophiles under mild base conditions. The tetrahydropyran acetal is generally stable under neutral/basic coupling conditions but can be cleaved under acidic conditions when deprotection is required, following established acetal chemistry principles.
* 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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