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Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside (CAS 27851-29-2)

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CAS Number:
27851-29-2
Molecular Weight:
540.65
Molecular Formula:
C34H36O6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside is a compound extensively studied in carbohydrate chemistry and organic synthesis. Its chemical structure, consisting of a glucose molecule with benzyl groups attached to the hydroxyl groups, lends itself to various synthetic applications. Researchers have utilized Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside as a versatile building block for the synthesis of complex carbohydrates and glycoconjugates. Due to the presence of multiple benzyl groups, this compound undergoes selective deprotection reactions, enabling the controlled removal of specific protecting groups to obtain desired intermediates or final products. Additionally, Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside has been employed as a substrate in enzymatic glycosylation reactions and glycosyltransferase assays to investigate enzyme kinetics and substrate specificity. Its compatibility with various reaction conditions and its stable chemical properties make it a valuable tool in the synthesis of carbohydrate-based molecules with potential applications in chemical biology, materials science, and drug discovery. Furthermore, researchers have explored the use of Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside in the development of glycosylation methodologies and the construction of glycan arrays for studying carbohydrate-protein interactions and glycobiology. Overall, Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside plays a crucial role in advancing our understanding of carbohydrate chemistry and has widespread applications in synthetic organic chemistry and chemical biology research.


Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside (CAS 27851-29-2) References

  1. An expedient synthesis of benzyl 2,3,4-tri-O-benzyl-beta-D-glucopyranoside and benzyl 2,3,4-tri-O-benzyl-beta-D-mannopyranoside.  |  Lu, W., et al. 2005. Carbohydr Res. 340: 1213-7. PMID: 15797138
  2. Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors.  |  Xie, W., et al. 2011. Bioorg Med Chem. 19: 2015-22. PMID: 21345683
  3. D-Glucose and D-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated D-glucose, D-mannose, and 2-deoxy-D-glucose.  |  Fokt, I., et al. 2013. Carbohydr Res. 368: 111-9. PMID: 23376241
  4. Synthesis and conformational analysis of d-gluco-pyranosyl-(6,6')-d-gluco-pyranuronate, a model compound for the inter-glycan 6,6'-ester linkage.  |  Hackbusch, S., et al. 2018. Carbohydr Res. 458-459: 1-12. PMID: 29428481
  5. Benzyl 2, 3, 4-tri-O-benzyl-β-D-glucopyranosiduronic acid and some related compounds  |  Zissis, E., & Fletcher Jr, H. G. 1970. Carbohydrate Research. 12(3): 361-368.
  6. Methyl 1, 2‐Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n‐Pent‐4‐enyl 1, 2‐Orthoesters  |  Uriel, C., Ventura, J., Gómez, A. M., López, J. C., & Fraser‐Reid, B. 2012. European Journal of Organic Chemistry. 2012(16): 3122-3131.
  7. A Novel Selectfluor-Mediated Regioselective O-Benzyl Ether Acetolysis of Perbenzylated Monosaccharides  |  Tambie, M. S., & Jalsa, N. K. 2015. Journal of Carbohydrate Chemistry. 34(9): 545-559.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Benzyl 2,3,4-Tri-O-benzyl-β-D-glucopyranoside, 25 mg

sc-221327
25 mg
$380.00