Date published: 2025-11-3

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2,3,4-Tri-O-acetyl-D-xylopyranose (CAS 106820-14-8)

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Alternate Names:
D-Xylose 2,3,4-Triacetate; 2,3,4-Tri-O-acetyl-D-xylose
Application:
2,3,4-Tri-O-acetyl-D-xylopyranose is used in the synthesis of D-xylopyranose series: tri-O-acetyl-D-xyloses and chloroacetyl derivatives.
CAS Number:
106820-14-8
Molecular Weight:
276.24
Molecular Formula:
C11H16O8
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2,3,4-Tri-O-acetyl-D-xylopyranose is a vital compound in carbohydrate chemistry research, offering insights into the synthesis and modification of complex sugars. The chemical mechanism involves the protection of specific hydroxyl groups on the xylopyranose ring, allowing for selective glycosylation reactions and the construction of diverse carbohydrate structures. Researchers utilize this compound to explore the structural and functional properties of xylose-containing oligosaccharides, elucidating their roles in biological processes such as cell-cell recognition, cell signaling, and host-pathogen interactions. Additionally, 2,3,4-Tri-O-acetyl-D-xylopyranose serves as a precursor in the synthesis of various glycoconjugates and glycosidic linkages, contributing to the development of glycoarrays and glycomaterials for applications in glycobiology, immunology, and biomaterials science. Its versatility extends to the study of carbohydrate-protein interactions, enzyme specificity, and carbohydrate-based targets, offering valuable insights into the design of novel carbohydrate-based drugs and vaccines. Overall, this chemical plays a crucial role in advancing our understanding of carbohydrate biology and its implications for diverse research fields, ranging from molecular biology to materials science.


2,3,4-Tri-O-acetyl-D-xylopyranose (CAS 106820-14-8) References

  1. Palladium-catalyzed oxidation of benzylated aldose hemiacetals to lactones.  |  Bessmertnykh, A., et al. 2004. Carbohydr Res. 339: 1377-80. PMID: 15113678
  2. Alkenyl and alkenoyl amphiphilic derivatives of D-xylose and their surfactant properties.  |  Damez, C., et al. 2007. Carbohydr Res. 342: 154-62. PMID: 17182017
  3. Palladium-catalyzed telomerization of butadiene with polyols: from mono to polysaccharides.  |  Bouquillon, S., et al. 2010. Top Curr Chem. 295: 93-119. PMID: 21626741
  4. Total Synthesis of Natural Disaccharide Sambubiose.  |  Lucarini, S., et al. 2020. Pharmaceuticals (Basel). 13: PMID: 32824527
  5. A convenient synthesis of 1-beta-D-arabinofuranosylthymine.  |  Keller, F. and Tyrrill, AR. 1966. J Org Chem. 31: 1289-91. PMID: 5907873
  6. Nucleosides and related substances. V. A synthetic procedure for nucleosides with the use of phosphorus pentoxide as dehydrating agent.  |  Onodera, K., et al. 1966. J Org Chem. 31: 1291-2. PMID: 5907874
  7. Palladium-Catalyzed Telomerization of Butadiene with Tri-O-acetylated Pentoses as a Convenient Route to 2,7-Octadienyl Glycosides  |  Hénin, F., Bessmertnykh, A., Serra‐Muns, A., Muzart, J., & Baillia, H. 2004. European Journal of Organic Chemistry. 2004(3): 511-520.
  8. Lactide polymerization co-initiated by carbohydrate esters and pyranoses  |  Tang, M., Haider, A. F., Minelli, C., Stevens, M. M., & Williams, C. K. 2008. Journal of Polymer Science Part A: Polymer Chemistry. 46(13): 4352-4362.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2,3,4-Tri-O-acetyl-D-xylopyranose, 100 mg

sc-213967
100 mg
$320.00