Cas no 946152-80-3 (Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate)

Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate is a chiral cyclopentane derivative featuring a benzyl ester group and a hydroxyl substituent at the 3-position. Its stereospecific (1r,3r) configuration makes it a valuable intermediate in asymmetric synthesis, particularly for pharmaceuticals and fine chemicals requiring precise stereochemistry. The hydroxyl group offers a reactive site for further functionalization, while the benzyl ester provides stability under various reaction conditions. This compound is useful in the synthesis of bioactive molecules, including prostaglandins and other cyclic frameworks. Its well-defined structure ensures reproducibility in research and industrial applications, making it a reliable choice for synthetic chemists.
Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate structure
946152-80-3 structure
Product Name:Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate
CAS No:946152-80-3
MF:C13H16O3
MW:220.264344215393
CID:1984617
PubChem ID:14530759
Update Time:2025-10-30

Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate Chemical and Physical Properties

Names and Identifiers

    • Benzyl (1R,3R)-3-hydroxycyclopentanecarboxylate
    • (1'R,3'aR,4'aR,8'aR,9'S,9'aS)-decahydro-1'-methyl-3'-oxo-spiro[1,3-dioxolane-2,6'(3'H)-naphtho[2,3-c]furan]-9'-carboxylic acid
    • FT-0673430
    • (1R,2S,8aR)-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone
    • 3-Oxo-(-)-lentiginosine
    • (1R,2S,8aR)-1,2-dihydroxy-hexahydroindolizin-3(5H)-one
    • CTK8E9690
    • (1R,3R)-3-hydroxy-cyclopentanecarboxylic acid benzyl ester
    • (1R,3R)-3-Hydroxycyclopentane carboxylic acid benzyl ester
    • A)]-Hexahydro-1,2-dihydroxy-3(2H)-indolizinone
    • A,2
    • A,8a
    • MFCD26407298
    • DB-257441
    • SCHEMBL2299968
    • AS-42467
    • PD019218
    • BENZYL (1R,3R)-3-HYDROXYCYCLOPENTANE-1-CARBOXYLATE
    • TRANS-BENZYL 3-HYDROXYCYCLOPENTANECARBOXYLATE
    • 946152-80-3
    • rel-benzyl (1R,3R)-3-hydroxycyclopentane-1-carboxylate
    • AKOS027332606
    • CS-0129392
    • 128095-32-9
    • Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate
    • MDL: MFCD26407298
    • Inchi: 1S/C13H16O3/c14-12-7-6-11(8-12)13(15)16-9-10-4-2-1-3-5-10/h1-5,11-12,14H,6-9H2/t11-,12-/m1/s1
    • InChI Key: RDUCOWDKAANTQZ-VXGBXAGGSA-N
    • SMILES: O[C@@H]1CC[C@@H](C(=O)OCC2C=CC=CC=2)C1

Computed Properties

  • Exact Mass: 220.109944368g/mol
  • Monoisotopic Mass: 220.109944368g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 233
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.8
  • Topological Polar Surface Area: 46.5?2

Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate Pricemore >>

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Additional information on Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate

Recent Advances in the Study of Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate (CAS: 946152-80-3) in Chemical Biology and Pharmaceutical Research

Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate (CAS: 946152-80-3) is a chiral cyclopentane derivative that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug development. This compound, characterized by its stereospecific hydroxyl and benzyl ester functional groups, serves as a versatile intermediate in the synthesis of bioactive molecules. Recent studies have explored its role in the development of novel therapeutics, particularly in the areas of anti-inflammatory agents, antiviral drugs, and enzyme inhibitors. The unique stereochemistry of this compound makes it a valuable scaffold for designing drugs with enhanced selectivity and reduced side effects.

One of the most notable advancements in the study of Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate is its application in the synthesis of prostaglandin analogs. Prostaglandins are lipid compounds with diverse physiological effects, and their synthetic analogs are widely used in treating conditions such as glaucoma and gastrointestinal ulcers. Researchers have demonstrated that the chiral center at the 3-position of the cyclopentane ring in Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate can be leveraged to produce prostaglandin analogs with improved pharmacokinetic properties. A 2023 study published in the Journal of Medicinal Chemistry highlighted the compound's utility in this context, showing that derivatives of this scaffold exhibited enhanced stability and bioavailability compared to traditional prostaglandin analogs.

In addition to its role in prostaglandin synthesis, Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate has been investigated as a precursor for antiviral agents. A recent study in Bioorganic & Medicinal Chemistry Letters reported the successful incorporation of this compound into the structure of novel nucleoside analogs, which demonstrated potent activity against RNA viruses, including SARS-CoV-2. The researchers attributed the antiviral efficacy to the compound's ability to mimic natural nucleosides while introducing steric hindrance that reduces viral enzyme recognition. This finding opens new avenues for developing broad-spectrum antiviral therapies.

Another promising area of research involves the use of Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate in enzyme inhibition. The compound's rigid cyclopentane backbone and functional groups make it an ideal candidate for designing inhibitors of enzymes such as cyclooxygenase (COX) and phosphodiesterase (PDE). A 2022 study in the European Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibited selective inhibition of COX-2, an enzyme implicated in inflammation and pain. The study also noted that the benzyl ester group could be readily modified to optimize binding affinity and selectivity, further underscoring the compound's versatility.

Despite these advancements, challenges remain in the large-scale synthesis and application of Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate. Recent efforts have focused on developing more efficient synthetic routes to produce the compound in high enantiomeric purity. A 2023 publication in Organic Process Research & Development described a novel catalytic asymmetric hydrogenation method that achieved >99% enantiomeric excess, significantly improving the yield and scalability of the synthesis. This breakthrough is expected to facilitate further research and commercialization of derivatives based on this scaffold.

In conclusion, Benzyl (1r,3r)-3-hydroxycyclopentanecarboxylate (CAS: 946152-80-3) represents a highly promising scaffold in chemical biology and pharmaceutical research. Its applications in prostaglandin synthesis, antiviral drug development, and enzyme inhibition highlight its versatility and potential for addressing unmet medical needs. Ongoing research aims to optimize its synthetic accessibility and explore new therapeutic applications, positioning this compound as a key player in the future of drug discovery.

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