THP-PEG10-OH , CAS No.42607-90-9

CAS: 42607-90-9 Cat. No.: T1445719 Formule: C₂₅H₅₀O₁₂ Poids moléculaire: 542.66

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

THP-PEG10-OH is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs.

Specifications

Conditions de stockage de stockage

Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Poids moléculaire

542.66

Application Protocols

Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule linker. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general procedural guidance.

Biological Roles

Biological roles below refer to general properties of PEG oligomers and THP-protected alcohols; they are not item-specific claims and are provided for research context only.

• PEG segment (literature): PEG chains create a dense hydration shell via hydrogen bonding, conferring “stealth” characteristics (reduced protein adsorption and aggregation) on surfaces and macromolecules. This underlies their routine use as spacers to minimize steric hindrance and nonspecific interactions in biochemical assays and surface functionalization.
• Spacer function (literature): a PEG10 length (~10 oxyethylene units) typically spans roughly 3–4 nm in an extended conformation in water, providing separation between a solid support or scaffold and a ligand/functional group to improve accessibility and reduce surface-induced effects.
• THP protection (literature): the THP end is stable at neutral pH, allowing biological buffer handling during conjugation at the free OH end. Under mild acidic conditions it deprotects to a diol, enabling subsequent functionalization steps without harsh reagents.
• Compatibility (literature): PEG oligomers are generally inert toward most biomolecules under neutral conditions and can increase aqueous solubility of attached hydrophobic moieties.

Note: No clinical or therapeutic claims are implied. Use is restricted to research applications.

Buffer Applications

This product is not a buffering agent and does not establish a defined pH range. Therefore, conventional buffer recipes (e.g., phosphate, HEPES, Tris) do not apply directly.

Practical guidance (literature):

• Handling in buffers: THP-PEG10-OH is compatible with neutral aqueous buffers for short exposures, but avoid acidic buffers if retention of the THP protecting group is required. Maintain pH ≥ 6.5–7.5.
• Co-solvents: to dissolve higher concentrations in aqueous buffers, add miscible co-solvents such as DMF or DMSO (1–20% v/v), ensuring final pH remains neutral.
• For planned deprotection: if removal of THP is desired, mildly acidic buffered media (e.g., acetate buffer pH ~4–5) with an organic co-solvent can be used under controlled conditions (literature).

Green Alternatives

Sustainability considerations for PEG-based linkers focus on solvent choice, protecting-group chemistry, and process intensification rather than replacing the PEG scaffold itself.

• PEG as a benign motif (literature): PEG oligomers are generally regarded as low-toxicity and biodegradable to varying extents, though complete mineralization may be slow. Their use can reduce reliance on halogenated auxiliaries by imparting solubility in greener solvents.
• Greener deprotection of THP (literature):
  • Use catalytic PPTS or citric acid in aqueous EtOH or 2-MeTHF rather than strong mineral acids in chlorinated solvents.
  • Conduct deprotection at ambient temperature to minimize energy input and side reactions.
• Solvent selection (literature): prioritize 2-MeTHF, CPME, EtOAc, MeOH/EtOH, or water/EtOH mixtures over DCM/DMF when feasible. For couplings, dimethyl carbonate can sometimes replace phosgene-derived reagents for carbonate formation.

Comparison of protecting groups (literature):

• THP ether: acid-labile, formed from DHP; deprotect under mild acid; moisture-tolerant during base-mediated steps.
• TBDMS ether: fluoride-labile; enables acid-compatible sequences but uses fluoride reagents and often chlorinated solvents.
• Acetals/benzylidene: also acid-labile but may require stronger conditions and generate aromatic byproducts.

Trade-offs: THP offers mild, catalytic acid deprotection and compatibility with many green solvents; however, its acid sensitivity can limit processing in acidic media. Choice depends on route and waste minimization targets.

Pharmaceutical Uses

No pharmacopeial status, excipient listing, or GMP grade is specified for this item; refer to CoA/Spec Sheet for any compliance designations.

General formulation/process roles of PEG oligomer linkers (literature; research/manufacturing context only):

• Solubilizing spacer: incorporation of short PEG chains into small molecules, affinity tags, or polymers increases aqueous compatibility and can improve processability in formulation development and analytical methods.
• Conjugation handle: the free OH can be converted to carbonate, carbamate, or ester linkages to attach the PEG spacer to APIs’ intermediates, affinity ligands, or surfaces used in purification.
• Surface passivation: PEGylated surfaces reduce fouling in process analytics and chromatography hardware; THP protection enables staged functionalization strategies.
• Crystallization aids: PEGylated auxiliaries sometimes modulate crystallization behavior of research intermediates due to altered polarity and hydrogen-bonding.

Important: This product is supplied strictly for research use only. No claims are made or implied for clinical, diagnostic, or therapeutic applications.

Physical Properties

The following item-specific physical constants are not provided in the product data for this SKU and should be confirmed on the CoA/Spec Sheet:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Exact molecular weight and formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, water content, residual solvents: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for THP-terminated PEG oligomers with n≈10:

• Physical state: often a waxy solid or high-viscosity syrup at ambient temperature; phase depends on dispersity and end-groups (literature).
• Solubility (literature): highly soluble/miscible with polar organic solvents (DCM, THF, acetone, MeOH, EtOH, DMF, DMSO). Soluble to miscible in water; THP end slightly reduces water solubility vs diol analog.
• Partitioning (literature): overall hydrophilic; logP not typically defined for oligomeric PEGs; expect strong hydrogen-bonding and high polarity.
• Hygroscopicity (literature): PEG oligomers can be hygroscopic and absorb atmospheric moisture; dry under vacuum when anhydrous conditions are required.
• Thermal behavior (literature): PEG oligomers soften with temperature; decomposition occurs before true boiling at ambient pressure; avoid prolonged heating above ~100–120°C to minimize acetal hydrolysis of the THP group.

Note: Treat any literature values/expectations as guidance only; do not apply as specifications for this item.

Quality and Grades

Item-specific grade/purity and stabilizer information were not provided in the product data for this SKU.

Guidance on grades for PEG-based linkers:

• Typical offerings include research grade (synthesis use), high-purity grade (for sensitive conjugations), and LC/MS grade (low nonvolatile residues). HPLC grade refers to solvents, not solid linkers; however, low-UV impurities are beneficial when monitoring reactions by UV.
• Purity considerations: oligomeric PEGs may be supplied as discrete n (monodisperse) or as narrow-dispersity distributions. Verify the “n=10” definition (discrete vs average) on the CoA. Side products can include lower/higher oligomers and residual protecting alcohols.
• Metal content, water content, and residual solvents: Not specified for this item; refer to CoA/Spec Sheet. For moisture-sensitive couplings, dryness is critical; pre-dry under high vacuum if needed.
• Stabilizers: PEG oligomers usually require no stabilizer. Acid-labile THP end-group stability is maximized by neutral storage conditions and absence of adventitious acids.
• What to verify on receipt: identity by NMR/FTIR (THP signals near 3.4–4.0 ppm complex multiplets; acetal signals circa 4.5–5.0 ppm), Mn/Mw by ESI-MS or MALDI (for discrete species), and absence of acidic contaminants (pH-neutral aqueous extract).

Reaction and Applications

THP-PEG10-OH functions as a hydrophilic spacer/linker with one protected terminus and one free hydroxyl, enabling stepwise syntheses and surface/bioconjugation workflows.

• Protecting-group strategy (literature): the THP terminus is acid-labile and can be removed selectively (PPTS, dilute mineral acids, or AcOH/H2O in organic co-solvent) to reveal a second alcohol, converting the oligomer into a diol for further derivatization.
• Linker installation (literature):
  • Convert the free OH to activated derivatives: tosylate/mesylate for nucleophilic substitution, CDI/DSC to carbonates for coupling to amines (urethane formation), or succinylation to introduce a terminal carboxyl for EDC/NHS couplings.
  • Urethane/urea linkages: react carbonate/isocyanate analogs with amines to append the PEG spacer to surfaces, polymers, or scaffolds.
• Materials and surface science: grafting to nanoparticles, oxides, or polymer backbones to improve dispersibility, reduce nonspecific adsorption, and adjust hydrophilicity.
• Combinatorial/solid-phase synthesis: PEG spacers reduce steric congestion and enhance solvation around reactive centers; the THP end ensures orthogonality to base-mediated transformations.
• Analytical handling: high polarity aids purification by reverse-phase methods; however, amphiphilicity can broaden peaks in normal-phase chromatography—gradient elution and low-UV detection are helpful.
• Practical tips: dry thoroughly prior to activation; maintain neutral to slightly basic conditions to preserve THP; avoid strong acids and prolonged heating.

Reaction Conditions

General literature guidance for common operations with THP-terminated PEG oligomers (values are typical ranges; optimize for your system):

• THP deprotection to diol:
  • Reagents: PPTS (5–10 mol%) or CSA (1–5 mol%) in MeOH, EtOH, or acetone/water; or AcOH/H2O in THF or 2-MeTHF.
  • Conditions: 20–40°C, 0.5–6 h depending on solvent and acid strength. Monitor by 1H NMR (loss of THP acetal signals ~4.5–5.0 ppm) or LC/MS.
• Tosylation of the free OH:
  • Reagents: TsCl (1.1–1.5 eq), Et3N or pyridine, catalytic DMAP in dry DCM or THF.
  • Conditions: 0–25°C, 1–4 h. Quench with aqueous bicarbonate; avoid strong acids.
• Carbonate formation (CDI):
  • Reagents: CDI (1.2–1.5 eq) in dry THF or DCM; then add amine nucleophile with base (Et3N).
  • Conditions: 0–25°C for activation (0.5–2 h); then 20–40°C for coupling (1–6 h).
• Succinylation to carboxylate:
  • Reagents: succinic anhydride (1.2–1.5 eq), DMAP (0.1 eq), Et3N in dry DCM/DMF.
  • Conditions: 20–30°C, 2–6 h.

Workup/purification tips (literature):

• Use minimal acid in silica chromatography; pre-neutralize silica with 1–2% Et3N in eluent if THP must be retained.
• Reverse-phase (C18) with water/acetonitrile gradients facilitates cleanup of salts and small-molecule byproducts; finish with lyophilization if aqueous miscible.

All conditions above are general literature guidance and not specifications for this item.

Safety and Handling

GHS/SDS information specific to this SKU was not provided in the product data. Always consult the product SDS for authoritative hazard classification and response instructions.

General safety guidance for THP-terminated PEG oligomers:

• Anticipated hazards (literature): low acute toxicity typical of PEGs; THP ethers are acetal-type protections that can hydrolyze under acidic conditions, generating alcohols. Avoid ingestion, inhalation of aerosols, and prolonged skin contact.
• Peroxide formation: not a known peroxide-forming class; nevertheless, observe routine precautions for ethers and store away from oxidizers.
• Incompatibilities: strong acids (promote THP deprotection/hydrolysis), strong oxidants (may oxidize ether backbone), strong bases at elevated temperature (can induce elimination/oxidation of PEG chains). Avoid moisture when anhydrous handling is needed.
• PPE: lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when heating, solvent handling, or performing reactions.
• First aid (overview; defer to SDS): skin—wash with soap and water; eyes—rinse cautiously with water for several minutes and seek medical attention if irritation persists; inhalation—move to fresh air; ingestion—rinse mouth, seek medical advice.
• Spill/cleanup: absorb viscous liquids with inert material, collect for disposal; wash residues with warm water/detergent; prevent release to drains during reaction workups containing organic solvents.
• Disposal: follow institutional and local regulations; PEG-containing waste and acidic deprotection mixtures should be collected as organic chemical waste.

Solvent Selection

As a PEG-based linker, THP-PEG10-OH is broadly compatible with polar organic solvents and, to a degree, with water.

• Polarity/miscibility (literature):
  • Miscible/soluble: DCM, chloroform, THF, acetone, MeOH/EtOH/i-PrOH, acetonitrile, DMF, DMSO.
  • Aqueous systems: soluble to highly soluble depending on temperature and ionic strength; the THP end slightly decreases water solubility vs the diol analog.
• Dielectric context (literature): PEG-rich media exhibit high effective dielectric constant, facilitating ionic reactions (e.g., carbodiimide couplings) without excessive salt.
• Selection tips:
  • Protecting-group chemistry (acid-labile THP): avoid protic acids in solvent systems unless deprotection is intended; neutral or buffered media are preferred for storage and coupling.
  • For carbonate/carbamate activation (e.g., CDI, DSC), use dry DCM, THF, or DMF. For tosylation/mesylation, employ dry DCM with pyridine or Et3N as base.
  • For bioconjugation in mixed aqueous media, co-solvents like DMF or DMSO improve handling and maintain THP stability at neutral pH.
• Quick comparison (literature):
  • DCM: excellent solubility, easy removal; avoid strong acid traces.
  • THF: good solubility; convenient for organometallic-free couplings; ensure dryness.
  • DMF/DMSO: maximize solubility for high loadings; more difficult to remove; ensure low water content for efficient activation.

Storage and Reconstitution

Item-specific storage and shipping:

• Storage conditions: Store at -20°C (per product data). Keep container tightly closed under inert atmosphere if possible to minimize moisture and acid uptake.
• Shipped in: Ice chest + ice pads (per product data).

General handling guidance (literature):

• Protect from moisture and acids to preserve the THP protecting group. Allow to warm to room temperature in a desiccator before opening to prevent condensation.
• If long-term storage is needed, aliquot under dry nitrogen or argon to minimize repeated freeze–thaw/open–close cycles. PEG oligomers can be viscous; warming to room temperature eases dispensing.
• Reconstitution/dissolution: dissolve in dry, neutral organic solvents such as DCM, THF, acetone, acetonitrile, DMF, or DMSO. For aqueous use, employ co-solvents and maintain neutral pH to avoid THP cleavage.
• Stability: avoid prolonged exposure to strong acids or elevated temperatures, which accelerate THP hydrolysis. For anhydrous reactions, consider pre-drying under high vacuum (room temp, 12–24 h) before use.

Research use only: not for human or veterinary use.

Structure and Identity

Item-specific identifiers provided: CAS 42607-90-9. Other identifiers are not provided in the product data for this specific item.

• Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

General/literature structural description (for THP-PEG10-OH):

• THP-PEG10-OH typically denotes a monofunctional polyethylene glycol oligomer containing ten oxyethylene units [–(CH2CH2O)10–], with one terminus protected as a tetrahydropyranyl (THP) ether and the other terminus as a free primary alcohol.
• Functional groups: polyether backbone (repeating –CH2–CH2–O–), one terminal tetrahydropyranyl acetal ether (a 6-membered saturated heterocycle, oxygen in ring), and one terminal primary hydroxyl.
• Topology: linear amphiphilic oligomer; the PEG chain is flexible and highly solvated; the THP end is acid-labile, enabling deprotection to a diol.
• Stereochemistry: none defined on the PEG chain; the THP group is typically substituted at C-2 (2-tetrahydropyranyl ether), which introduces no fixed stereocenter in the acetal as supplied.
• 2D depiction in words: THP–O–(CH2–CH2–O)×10–CH2–CH2–OH, where THP is a 2-tetrahydropyranyl ring attached via the ring oxygen to the terminal PEG oxygen.

Synthetic Utility

THP-PEG10-OH offers orthogonal reactivity: a protected, acid-labile THP terminus and a free primary alcohol, enabling sequential diversification.

Key transformations (literature):

• Activation of the free OH:
  • Tosylation/mesylation to give leaving groups for SN2 substitution with nucleophiles (azide, halides, thiols, amines).
  • Carbonate formation via CDI or DSC, enabling urethane formation with amines under mild base.
  • Esterification (e.g., with succinic anhydride) to introduce a terminal carboxyl for EDC/NHS coupling.
• Post-substitution conversions: azide → amine (Staudinger or catalytic hydrogenation) to generate amine-terminated PEGs; halide → thiol via thiourea; thiol → maleimide conjugation after further derivatization.
• THP deprotection: catalytic acid (PPTS, CSA) in alcohol or aprotic solvent/water mixtures to expose the second OH, allowing symmetric/unsymmetric diol elaborations (e.g., selective mono-activation strategies using protecting-group orthogonality).
• Surface and polymer modification: grafting to oxides or polymers through silane/urethane/ester chemistry after suitable end-group conversion.

Practical notes: maintain anhydrous conditions during activation to maximize conversions; neutralize/remove acids before work-up to preserve THP; use excess base scavengers (Et3N, pyridine) to minimize acetal cleavage during sulfonylations.

Target Specificity

Not applicable. This product is a small-molecule PEG linker, not a biological targeting reagent or antibody. No target, clone, isotype, or species reactivity applies.

Foire aux questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 42607-90-9, the molecular formula is C25H50O12, and the molecular weight is 542.66 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.