127751-08-0

Basic information

• Product Name: Tetrakis(2-propynyloxymethyl) methane
• Synonyms: Tetrakis(2-propynyloxymethyl) methane;3,3'-[[2,2-bis[(2-propyn-1-yloxy)methyl]-1,3-propanediyl]bis(oxy)]bis-1-Propyne;1,3-bis(prop-2-ynoxy)-2,2-bis(prop-2-ynoxymethyl)propane
• CAS NO: 127751-08-0
• Molecular Formula: C₁₇H₂₀O₄
• Molecular Weight: 288
• Mol File: 127751-08-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly, Sonicated)
• CAS DataBase Reference: Tetrakis(2-propynyloxymethyl) methane(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrakis(2-propynyloxymethyl) methane(127751-08-0)
• EPA Substance Registry System: Tetrakis(2-propynyloxymethyl) methane(127751-08-0)

Safety Data

• Hazardous Substances Data: 127751-08-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tetrakis(2-propynyloxymethyl) methane is used as a key intermediate in the synthesis of Aminoglycoside Cyclic Oligosaccharides. These compounds serve as multimeric Pand E-selectin antagonists, which play a crucial role in various biological processes, including cell adhesion, inflammation, and immune response regulation. By targeting these selectins, these antagonists have the potential to be developed into therapeutic agents for treating conditions such as autoimmune diseases, inflammatory disorders, and cancer.

Upstream product

• 115-77-5 Pentaerythritol 
• 106-96-7 propargyl bromide 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 1453118-16-5 C₁₀₅H₁₄₄N₂₀O₄₀ 

Relevant articles and documents

Star polymers by photoinduced copper-catalyzed azide-alkyne cycloaddition click chemistry

Well-defined star polymers consisting of tri-, tetra-, or octa-arms have been prepared via coupling-onto strategy using photoinduced copper(I)-catalyzed 1,3-dipolar cycloaddition click reaction. An azide end-functionalized polystyrene and poly(methyl meth

Multimeric xanthates as carbonic anhydrase inhibitors

The field of multivalent inhibition of enzymes is growing exponentially from the first reported multivalent effect on a glycosidase enzyme. However, the investigations have generally remained restricted to carbohydrate-processing enzymes. Carbonic anhydrases are ubiquitous metallo-enzymes involved in many key biological processes, that catalyze the reversible hydration/dehydration of CO2/HCO3. This study reports the first synthesis of multimeric xanthates addressing the selectivity and potency of CA multivalent inhibition. Six multivalent compounds containing three, four, and six xanthate moieties were prepared and assayed against four relevant CA isoforms together with their monovalent analogues. Some of the multimers were stronger inhibitors than the monomeric species. For hCA I, the two best molecules 18 and 20 showed an improvement of the ligand affinity of 4.8 and 2.3 per xanthate units (valence-corrected values), respectively, which corresponds to a clear multivalent effect. Moreover, the biochemical assays demonstrated that the multimeric presentation of xanthates, also affected the selectivity of the relative inhibition among the four CAs assayed.

Sliding-graft interpenetrating polymer networks from simultaneous "Click Chemistry" and atom transfer radical polymerization

In this work, a kind of semi-interpenetrating polymer network (s-IPN) with unique molecular structures, poly(ethylene glycol) (PEG) network with movable sliding-grafted poly(2-hydroxyethyl methacrylate) (PHEMA) (sIPN-PEG/α -CD-sg- PHEMA), were first reported. sIPN-PEG/α -CD-sg-PHEMAs were prepared by simultaneous "click chemistry" and atom transfer radical polymerization (ATRP) of a mixture of poly(ethylene glycol)-diazide/ bromobutyryloxy R-cyclodextrin inclusion complex (N3-PEGN3/( R-CD-BIBB)m), tetrakis(2-propynyloxymethyl) methane (TMOP), CuBr, pentamethyldiethylenetriamine (PMDETA), HEMA and DMF. Attributable to the controlled characters of ATRP and the quantitative yields of "click chemistry", the prepared sIPN-PEG/α -CD-sg-PHEMAs have the well-defined PEG networks, as well as uniform and tunable sliding-grafted PHEMA chains. The length of sliding-grafted PHEMA of the sIPN-PEG/α -CD-sg-PHEMA can be regulated by changing polymerization times. The molecular structures, and physical and thermal properties of the sIPN-PEG/α -CD-sg-PHEMA were studied by FTIR, 1HNMR, XPS, TGA, and DSC measurements. The sIPN-PEG/α -CD-sg-PHEMAs exhibit good physical and mechanical properties. Most important, comparing to classical semi-IPN, the diffusion of interpenetrated PHEMA from sIPN-PEG/α -CD-sg-PHEMA was largely prevented for a long time solvent immersion because the PHEMA brushes were fixed on PEG networks. The sliding-grafted PHEMA chains afford functionalities to the bulk and surface of s-IPN-PEG and could potentially be used as carriers of genes and drugs.

Well-defined biodegradable amphiphilic conetworks

A series of amphiphilic conetworks (APCNs) with well-defined molecular structures were prepared via a copper-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC) of tetrakis(2-propynyloxymethyl)methane (TMOP), diazide end-functionalized triblock copolymers of poly(ε-caprolactone) with poly(ethylene glycol) (N3-PCL-PEG-PCL-N3). The so-prepared APCNs exhibit unique properties of ordered nanophase separation of hydrophilic (HI) and hydrophobic (HO) phases, and a variable swelling capacity both in water and organic solvent. The morphology, surface properties and thermal behavior of the APCNs were investigated by scanning electron microscopy (SEM), water contact angle (WCA), and differential scanning calorimetry (DSC), respectively. The physical properties of APCNs depended on the ratio of HI-HO, which can be regulated via precise synthesis of N3-PCL-PEG-PCL-N3. The analysis of an in vitro cell viability assay suggests that the APCNs have excellent biocompatibility. The prepared APCNs are excellent carriers for controlled drug release. The hydrophilic choline theophyllinate and hydrophobic 5-fluorouracil (5-FU) were loaded into the APCNs simultaneously as model drugs to study the release from APCNs. The well-controlled drug release is attributable to the well-defined molecular structure and tunable HI/HO composition of the APCNs.

A water-soluble AIE-active polyvalent glycocluster: Design, synthesis and studies on carbohydrate-lectin interactions for visualization of Siglec distributions in living cell membranes

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Figure-Eight-Shaped and Cage-Shaped Cyclic Polystyrenes

Nonlinear polystyrenes (PS) with similar molecular weights but with different molecular structures having star-, figure-8-, and cage-shaped architectures were synthesized by combining atom transfer radical polymerization (ATRP) and click chemistry. Figure-8- and cage-shaped PS were fractionated by using a gradient normal phase liquid chromatography as confirmed by SEC-LS, MALDI-TOF MS, 1H NMR, and FT-IR spectrometry. Their purities were estimated by using a two-dimensional liquid chromatography (2D-LC). The glass transition temperatures of these topologically different polymers were in the order of cage-, figure-8-, and star-shaped polymers possibly due to the multiple links that constrain the overall molecular diffusivity in the case of multicyclic polymers (figure-8, and cage). Monte Carlo simulation on the glass transition behavior of model system also agreed well with the experimental results.

Telodendrimer-Based Macromolecular Drug Design using 1,3-Dipolar Cycloaddition for Applications in Biology

An architectural polymer containing hydrophobic isoxazole-based dendron and hydrophilic polyethylene glycol linear tail is prepared by a combination of the robust ZnCl2 catalyzed alkyne-nitrile oxide 1,3-dipolar cycloaddition and esterification chemistry. This water soluble amphiphilic telodendrimer acts as a macromolecular biologically active agent and shows concentration dependent reduction of glioblastoma (U251) cell survival.

Synthesis and encapsulation of an amphiphilic thermoresponsive star polymer with β-cyclodextrin and hyperbranched poly(oligo(ethylene glycol)methacrylate) as building blocks

Novel macromolecular star polymers with triazole and cyclodextrin (CD) segments as branch points and poly(oligo(ethylene glycol)methacrylate) (POEGMAs) as dense hydrophilic branches were synthesized via a combination of azide-alkyne click chemistry and at

Cluster glycosides and heteroglycoclusters presented in alternative arrangements

Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose

Interpenetrating network hydrogels via simultaneous "click Chemistry" and atom transfer radical polymerization

Simultaneous interpenetrating polymer networks (sIPNs) from concurrent copper(I)-catalyzed azide-alkyne cycloaddition "click chemistry" and atom transfer radical polymerization (ATRP) are described. Semi-sIPN of poly(ethylene glycol)/poly(2-hydroxyethyl methacrylate) (semi-PEG/PHEMA-sIPN) was first prepared via simultaneous "click chemistry" and ATRP from a mixture of poly(ethylene glycol)-diazide (N3-PEG-N3, Mn = 4000 g/mol), tetrakis(2-propynyloxymethyl)methane (TPOM), ethyl-2-bromobutyrate (EBB), CuBr, pentamethyldiethylenetriamine (PMDETA), and 2-hydroxyethyl methacrylate (HEMA) in dimethylformamide (DMF). Full sIPN of PEG/PHEMA (full-PEG/PHEMA-sIPN) was then prepared via simultaneous "click chemistry" and ATRP from a mixture of N3-PEG-N3 (Mn = 4000 g/mol), TPOM, EBB, CuBr, PMDETA, HEMA, and poly(ethylene glycol) diacrylate) (PEGDA, Mn = 575) in DMF. Both the semi- and full-sIPNs exhibit a fast gelation rate and high gel yield. The sIPNs also exhibit high swelling ratios and good mechanical and antifouling properties. The morphology and thermal behavior of the sIPNs were studied by scanning electron microscopy (SEM), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). These sIPNs could find applications as biomaterials for contact lenses, biomedical materials, artificial organs, and drug delivery systems.