2-(Tetrahydro-2H-pyran-2-yloxy)ethanol - CAS 2162-31-4

Inquiry

2-(Tetrahydro-2H-pyran-2-yloxy)ethanol is a polyethylene glycol (PEG)-based PROTAC linker that can be used in the synthesis of a series of PROTACs.

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Molecular Formula

C7H14O3

Molecular Weight

146.18

2-(Tetrahydro-2H-pyran-2-yloxy)ethanol

- Specification
  - Related CAS
    
    92417-25-9 (polymer) 301295-36-3 (polymer)
    
    Purity
    
    ≥95%
    
    Solubility
    
    Soluble in Acetone, Chloroform (Slightly), Dichloromethane, Ethyl Acetate (Slightly)
    
    Appearance
    
    Clear Colorless Oily Matter
    
    Storage
    
    Store at 2-8°C
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    2-(oxan-2-yloxy)ethanol
    
    Synonyms
    
    OH-PEG1-THP; HO-PEG1-THP; Tetrahydropyranylethyleneglycol; 1-Hydroxy-2-(2-tetrahydropyranyloxy)ethane; 2-(2-Hydroxyethoxy)tetrahydropyran; Ethylene Glycol Mono(tetrahydropyranyl Ether); THP-PEG1-alcohol; 2-((tetrahydro-2H-pyran-2-yl)oxy)ethan-1-ol; Ethanol, 2-[(tetrahydro-2H-pyran-2-yl)oxy]-; 2-(Tetrahydro-pyran-2-yloxy)-ethanol
- Properties
  - Boiling Point
    
    95°C at 22 mmHg
    
    Density
    
    1.077 g/mL at 20°C
    
    InChI Key
    
    XDBZJXRPEKFIFR-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C7H14O3/c8-4-6-10-7-3-1-2-5-9-7/h7-8H,1-6H2
    
    Canonical SMILES
    
    C1CCOC(C1)OCCO
- Reference Reading
  - 1. Versatile and selective synthesis of "click chemistry" compatible heterobifunctional poly(ethylene glycol)s possessing azide and alkyne functionalities
    
    Shigehiro Hiki, Kazunori Kataoka Bioconjug Chem. 2010 Feb 17;21(2):248-54. doi: 10.1021/bc900253p.
    
    Versatile route for "click chemistry" compatible heterobifunctional PEGs was established through preparation of alpha-tetrahydropyranyloxy-omega-hydroxyl poly(ethylene glycol) (THP-PEG-OH) via ring-opening polymerization of ethylene oxide using 2-(tetrahydro-2H-pyran-2-yloxy)ethanol as an initiator, followed by the functionalization of omega-OH group to either the azido or alkyne group. Quantitative azidation of THP-PEG-OH was confirmed from the analysis of molecular functionality of the derivatives. While the conversion efficiency of omega-alkynation was appropriately 70%, the unreacted THP-PEG-OH fraction was successfully removed by ion-exchange chromatography after the carboxylation of the hydroxyl group with succinic anhydride. Then, the protecting group of the alpha-end, THP, was removed in mild acidic media, followed by two- or three-step modification of the resulting alpha-hydroxyl group to primary amino or thiol groups. Consequently, "click chemistry" compatible heterobifunctional PEG derivatives (X-PEG-Y; X = NH(2) and SH, Y =Azide and Alkyne) were synthesized with high efficiency and controlled molecular weight.

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