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4,6-O-Benzylidene-D-glucose (CAS 30688-66-5)

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Alternate Names:
4,6-O-(phenylmethylene)-D-glucose
Application:
4,6-O-Benzylidene-D-glucose is an intermediate for the synthesis of carbohydrates
CAS Number:
30688-66-5
Purity:
≥98%
Molecular Weight:
268.26
Molecular Formula:
C13H16O6
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-glucose is a key compound in carbohydrate chemistry research, primarily employed as a protecting group for the hydroxyl functional groups present in glucose molecules. The benzylidene group selectively protects the C4 and C6 hydroxyl groups, leaving the remaining hydroxyl groups free for further manipulation. This chemical plays a crucial role in the synthesis of various carbohydrate derivatives and glycoconjugates, serving as a versatile building block in the assembly of complex carbohydrate structures. Researchers utilize 4,6-O-benzylidene-D-glucose in the synthesis of oligosaccharides, glycopeptides, and glycolipids, enabling the investigation of carbohydrate-protein interactions, molecular recognition events, and the development of carbohydrate-based materials. Additionally, this compound has been employed in the modification of natural carbohydrates to enhance their stability, solubility, and bioactivity. Its chemical stability and compatibility with a wide range of synthetic transformations make it a valuable tool for the efficient synthesis of diverse carbohydrate derivatives with tailored structures and properties. Furthermore, 4,6-O-benzylidene-D-glucose contributes to advancing our understanding of carbohydrate biology and facilitates the development of novel carbohydrate-based materials with potential applications in biotechnology, materials science, and drug delivery systems.


4,6-O-Benzylidene-D-glucose (CAS 30688-66-5) References

  1. Stereocontrolled synthesis of fully functionalized D-glucosamine monosaccharides via a domino nitro-Michael/Henry reaction.  |  Adibekian, A., et al. 2008. Chem Commun (Camb). 3549-51. PMID: 18654709
  2. Effect on protein synthesis and cell survival of the benzaldehyde derivatives sodium benzylidene ascorbate (SBA) and the deuterated compound zilascorb(2H).  |  Pettersen, EO., et al. 1991. Anticancer Res. 11: 1077-81. PMID: 1888141
  3. 985. Aspects of stereochemistry. Part VIII. Determination of the configuration at the benzylidene acetal carbon atoms in 4, 6-O-benzylidene-D-glucose and 1, 3-O-benzylidene-L-arabinitol by nuclear magnetic resonance spectroscopy[J].  |  Foster A B, Haines A H, Homer J,. 1961: Journal of the Chemical Society (Resumed),. 5005-5011.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4,6-O-Benzylidene-D-glucose, 5 g

sc-284473
5 g
$80.00

4,6-O-Benzylidene-D-glucose, 10 g

sc-284473A
10 g
$120.00