Date published: 2025-12-13

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Tri-O-acetyl-D-glucal (CAS 2873-29-2)

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Application:
Tri-O-acetyl-D-glucal is a derivative of D-glucal
CAS Number:
2873-29-2
Molecular Weight:
272.25
Molecular Formula:
C12H16O7
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Tri-O-acetyl-D-glucal is a chemical compound of interest in scientific research due to its versatile applications in organic synthesis and carbohydrate chemistry. This compound serves as a valuable building block for the synthesis of various complex organic molecules, including carbohydrates, glycoconjugates, and natural products. One of its key research applications lies in its role as a precursor in the synthesis of carbohydrate derivatives and glycosylation reactions. Tri-O-acetyl-D-glucal can undergo selective deacetylation to yield the corresponding glycosyl acceptors, which can then participate in glycosylation reactions catalyzed by glycosyltransferases. Moreover, its unique reactivity allows for the selective functionalization of the anomeric position, enabling the introduction of diverse functional groups and modifications into carbohydrate scaffolds. Additionally, Tri-O-acetyl-D-glucal serves as a valuable starting material for the preparation of glycosyl donors, glycosyl halides, and glycosyl triflates, which are essential intermediates in the synthesis of oligosaccharides and glycoconjugates with defined structures. Furthermore, its involvement in the synthesis of natural products, pharmaceutical intermediates, and carbohydrate-based materials underscores its significance in chemical biology, medicinal chemistry, and materials science research. Overall, Tri-O-acetyl-D-glucal plays a pivotal role as a versatile synthetic building block and a key reagent in carbohydrate chemistry, facilitating the exploration of carbohydrate structure-function relationships, the development of novel synthetic methodologies, and the synthesis of biologically active molecules with potential applications in various research fields.


Tri-O-acetyl-D-glucal (CAS 2873-29-2) References

  1. Synthesis of enantiopure 3-azabicyclo[3.3.0]octen-7-one derivatives via intramolecular Pauson-Khand cycloaddition reaction using tri-O-acetyl-D-glucal as starting material.  |  Areces, P., et al. 2002. J Org Chem. 67: 3506-9. PMID: 12003568
  2. The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides.  |  Liberek, B., et al. 2002. Carbohydr Res. 337: 1803-10. PMID: 12431882
  3. Synthesis of novel migrastatin and dorrigocin A analogues from D-glucal.  |  Anquetin, G., et al. 2008. Chemistry. 14: 1592-600. PMID: 18038383
  4. A one-step C-linked disaccharide synthesis from carbohydrate allylsilanes and tri-O-acetyl-D-glucal.  |  de Raadt, A. and Stütz, AE. 1991. Carbohydr Res. 220: 101-15. PMID: 1811852
  5. The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of omega-aminoalkyl 2-deoxy- and 2,3-dideoxy-d-hexopyranosides.  |  Pierwocha, AW. and Walczak, K. 2008. Carbohydr Res. 343: 2680-6. PMID: 18760404
  6. An efficient method for the selective synthesis of 2-deoxy-2-iodo-glycosides by O-glycosidation of D-glucal using I₂-Cu(OAc)₂.  |  Sirion, U., et al. 2010. Carbohydr Res. 345: 2401-7. PMID: 20880519
  7. Enantioselective Synthesis of a Cyclopropane Derivative of Spliceostatin A and Evaluation of Bioactivity.  |  Ghosh, AK., et al. 2018. Org Lett. 20: 7293-7297. PMID: 30394756
  8. Design and synthesis of herboxidiene derivatives that potently inhibit in vitro splicing.  |  Ghosh, AK., et al. 2021. Org Biomol Chem. 19: 1365-1377. PMID: 33480941
  9. A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation.  |  Gómez, AM., et al. 2021. J Org Chem. 86: 9181-9188. PMID: 34156858
  10. UV degradation of poly(lactic acid) materials through copolymerisation with a sugar-derived cyclic xanthate.  |  Hardy, C., et al. 2022. Chem Commun (Camb). 58: 5463-5466. PMID: 35416817

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Tri-O-acetyl-D-glucal, 5 g

sc-222367
5 g
$300.00