Cas no 204509-08-0 ((3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol)

(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol is a chiral diol compound featuring hydroxymethyl and hydroxyl functional groups on a tetrahydrofuran backbone. Its stereospecific (3S,5S) configuration makes it a valuable intermediate in asymmetric synthesis, particularly for pharmaceuticals and fine chemicals. The presence of two hydroxyl groups enhances its utility as a building block for complex molecular architectures, enabling selective derivatization. Its tetrahydrofuran ring structure contributes to stability while maintaining reactivity for further functionalization. This compound is particularly useful in the synthesis of biologically active molecules, where stereochemical precision is critical. Its balanced hydrophilicity and structural rigidity make it suitable for applications in medicinal chemistry and material science.
(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol structure
204509-08-0 structure
Product Name:(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol
CAS No:204509-08-0
MF:C5H10O3
MW:118.131102085114
MDL:MFCD11617839
CID:1034729
PubChem ID:10796728
Update Time:2025-11-01

(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol Chemical and Physical Properties

Names and Identifiers

    • (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol
    • (3S,5S)-5-(hydroxymethyl)oxolan-3-ol
    • (2S, 4S)-4-HYDROXYTETRAHYDROFURAN-2-METHANOL
    • AK131139
    • FCH890283
    • FCH3618736
    • RL02538
    • AX8252062
    • (2S,4S)-2-(Hydroxymethyl)tetrahydrofuran-4-ol
    • A919691
    • 204509-08-0
    • CS-0316360
    • AKOS016844292
    • DTXSID90444914
    • J-501296
    • SCHEMBL8220002
    • DS-6849
    • C73873
    • (3S, 5S)-5-(hydroxymethyl)oxolan-3-ol
    • DB-289923
    • MDL: MFCD11617839
    • Inchi: 1S/C5H10O3/c6-2-5-1-4(7)3-8-5/h4-7H,1-3H2/t4-,5-/m0/s1
    • InChI Key: WDMXOLOBWMBITN-WHFBIAKZSA-N
    • SMILES: O1C[C@H](C[C@H]1CO)O

Computed Properties

  • Exact Mass: 118.062994177g/mol
  • Monoisotopic Mass: 118.062994177g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 1
  • Complexity: 74.1
  • 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
  • Topological Polar Surface Area: 49.7
  • XLogP3: -1

Experimental Properties

  • Boiling Point: 275.1±15.0°C at 760 mmHg

(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol Security Information

(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol Pricemore >>

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Additional information on (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol

(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol (CAS No. 204509-08-0): A Comprehensive Overview

(3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol (CAS No. 204509-08-0) is a chiral organic compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound is characterized by its unique stereochemistry and functional groups, making it a valuable building block for the synthesis of various bioactive molecules and pharmaceuticals.

The molecular formula of (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol is C6H12O3, and its molecular weight is approximately 132.16 g/mol. The compound features a tetrahydrofuran ring with a hydroxymethyl group at the C-5 position and a hydroxyl group at the C-3 position. The specific stereochemistry of this compound, denoted by the (3S,5S) configuration, imparts unique chemical and biological properties that are crucial for its applications in various scientific and industrial processes.

In recent years, (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol has been extensively studied for its potential as an intermediate in the synthesis of pharmaceuticals and bioactive compounds. One notable application is in the development of antiviral agents. Research published in the Journal of Medicinal Chemistry highlighted the use of this compound as a key intermediate in the synthesis of novel antiviral drugs targeting RNA viruses such as influenza and SARS-CoV-2. The chiral centers in (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol play a critical role in ensuring the correct stereochemical configuration of the final drug molecules, which is essential for their biological activity and efficacy.

Beyond antiviral applications, (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol has also shown promise in the synthesis of anti-cancer agents. A study published in Cancer Research demonstrated that derivatives of this compound exhibit potent cytotoxic activity against various cancer cell lines. The hydroxyl groups on the tetrahydrofuran ring can be functionalized to introduce different substituents, leading to a diverse array of compounds with varying biological activities. This versatility makes (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol an attractive starting material for drug discovery efforts.

The synthetic routes to (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol have been optimized to improve yield and stereoselectivity. One common approach involves the asymmetric reduction of a suitable precursor followed by ring closure to form the tetrahydrofuran ring. Recent advancements in catalytic asymmetric synthesis have further enhanced the efficiency and scalability of these processes. For instance, a study published in Organic Letters reported a highly efficient method using a chiral catalyst to achieve high enantioselectivity in the synthesis of (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol.

In addition to its role as a synthetic intermediate, (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol has been explored for its potential as a biomarker in diagnostic applications. Research published in Biochemical Journal investigated the use of this compound as a marker for specific metabolic pathways or disease states. The unique chemical structure and reactivity of (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol make it suitable for developing sensitive and selective detection methods.

The safety profile of (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol has also been evaluated to ensure its suitability for various applications. Toxicological studies have shown that this compound exhibits low toxicity when used under controlled conditions. However, proper handling and storage protocols should be followed to minimize any potential risks associated with its use.

In conclusion, (3S,5S)-5-(Hydroxymethyl)tetrahydrofuran-3-ol (CAS No. 204509-08-0) is a versatile and valuable compound with diverse applications in pharmaceutical research and development. Its unique stereochemistry and functional groups make it an ideal candidate for the synthesis of bioactive molecules with therapeutic potential. Ongoing research continues to uncover new uses and properties of this compound, further solidifying its importance in the scientific community.

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