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4,6-O-Benzylidene-D-glucal (CAS 14125-70-3)

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Application:
4,6-O-Benzylidene-D-glucal is a derivative of D-glucal
CAS Number:
14125-70-3
Purity:
≥98%
Molecular Weight:
234.25
Molecular Formula:
C13H14O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4,6-O-Benzylidene-D-glucal is a chemical compound used extensively in carbohydrate chemistry and organic synthesis research. Its mechanism of action is based on its unique chemical structure, featuring a benzylidene moiety attached to the 4 and 6 positions of the glucal ring. This structural modification imparts specific properties to the compound, making it a versatile building block for the synthesis of various carbohydrate derivatives and glycoconjugates. Researchers employ 4,6-O-Benzylidene-D-glucal in the preparation of complex carbohydrate structures, such as glycosides, glycopeptides, and glycolipids, through chemical and enzymatic transformations. Additionally, this compound serves as a precursor for the synthesis of diverse glycan motifs, enabling investigations into the roles of carbohydrates in biological recognition processes, such as cell-cell interactions, microbial pathogenesis, and immune responses. Furthermore, 4,6-O-Benzylidene-D-glucal finds applications in the development of carbohydrate-based materials and biomimetic systems for drug delivery, tissue engineering, and diagnostics. Its facile chemical manipulability and compatibility with various synthetic methodologies make it an invaluable tool for advancing our understanding of carbohydrate structure-function relationships and exploring their applications in biotechnology, materials science, and chemical biology research.


4,6-O-Benzylidene-D-glucal (CAS 14125-70-3) References

  1. Stereoselective synthesis of a C-glycosylic compound (a 'methyl C-glycoside') through a regioselective free-radical ring-opening reaction. A single-crystal X-ray structure determination.  |  Shanmugasundaram, B., et al. 2002. Carbohydr Res. 337: 1523-27. PMID: 12350320
  2. A facile synthesis of 4,6-O-benzylidene-D-glycals via 1,5-anhydro-4,6-O-benzylidene-D-hex-1-en-3-ulose.  |  Sakakibara, T., et al. 2008. Carbohydr Res. 343: 2740-3. PMID: 18558400
  3. Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives.  |  Watanabe, Y., et al. 2009. Carbohydr Res. 344: 516-20. PMID: 19185852
  4. Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups.  |  Padungros, P., et al. 2014. J Org Chem. 79: 2611-24. PMID: 24548247
  5. Epimerization of glycal derivatives by a cyclopentadienylruthenium catalyst: application to metalloenzymatic DYKAT.  |  Lihammar, R., et al. 2014. Chemistry. 20: 14756-62. PMID: 25234515
  6. Synthesis and Antiproliferative Evaluation of 2-Deoxy-N-glycosylbenzotriazoles/imidazoles.  |  Garton, CS., et al. 2021. Molecules. 26: PMID: 34205324
  7. Palladium-Catalyzed O-Glycosylation through π-π Interactions.  |  Sun, Y., et al. 2024. Org Lett.. PMID: 38870323
  8. Recent developments in the Ferrier rearrangement[J].  |  Gómez A M, Lobo F, Uriel C. 2013,. European Journal of Organic Chemistry,. 2013(32):: 7221-7262.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4,6-O-Benzylidene-D-glucal, 100 mg

sc-284472
100 mg
$130.00

4,6-O-Benzylidene-D-glucal, 250 mg

sc-284472A
250 mg
$200.00