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1,6-Anhydro-β-D-mannopyranose (CAS 14168-65-1)

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Alternate Names:
1,6-Anhydromannose; Mannosan
Application:
1,6-Anhydro-β-D-mannopyranose is an anhydro sugar
CAS Number:
14168-65-1
Molecular Weight:
162.14
Molecular Formula:
C6H10O5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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1,6-Anhydro-β-D-mannopyranose, known as levoglucosan, is a specialized organic compound belonging to the class of anhydro sugars. This compound is characterized by its unique structural feature, which includes the formation of an anhydro bridge between the 1st and 6th carbon atoms of the mannopyranose molecule. This bridging results in a cyclic ether that is a key intermediate in various chemical synthesis processes and research applications, particularly in the study of carbohydrate chemistry and pyrolysis reactions. The formation of 1,6-Anhydro-β-D-mannopyranose is of significant interest in the investigation of biomass combustion and pyrolysis, serving as a marker for these processes due to its formation from the thermal degradation of cellulose and other polysaccharides. In research applications, it is often utilized as a starting material for the synthesis of complex carbohydrates and glycoconjugates, exploiting its reactive sites for glycosylation reactions that are in the assembly of oligosaccharides and polysaccharides with specific and controlled structures. Moreover, the study of 1,6-Anhydro-β-D-mannopyranose contributes to the understanding of the chemical behavior of sugars under thermal stress and their transformation pathways, which is essential for developing biofuels and understanding the chemistry underlying biomass conversion technologies. Its role in synthetic chemistry extends to the exploration of novel methodologies for the selective functionalization of carbohydrates, aiming at the development of new materials, bioactive compounds, and analytical tools based on sugar derivatives.


1,6-Anhydro-β-D-mannopyranose (CAS 14168-65-1) References

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  2. Three 1,6-anhydro-beta-D-glycopyranose derivatives.  |  Foces-Foces, C. 2001. Acta Crystallogr C. 57: 298-301. PMID: 11250585
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  4. Stereoselective (2-naphthyl)methylation of sugar hydroxyls by the hydrogenolysis of diastereoisomeric dioxolane-type (2-naphthyl)methylene acetals.  |  Borbás, A., et al. 2002. Carbohydr Res. 337: 1941-51. PMID: 12433460
  5. Development of a gas chromatographic/ion trap mass spectrometric method for the determination of levoglucosan and saccharidic compounds in atmospheric aerosols. Application to urban aerosols.  |  Pashynska, V., et al. 2002. J Mass Spectrom. 37: 1249-57. PMID: 12489085
  6. Synthesis of hyperbranched carbohydrate polymers by ring-opening multibranching polymerization of anhydro sugar.  |  Satoh, T. and Kakuchi, T. 2007. Macromol Biosci. 7: 999-1009. PMID: 17595682
  7. Inverted regioselectivity of C-H amination: Unexpected oxidation at beta- rather than gamma-C-H.  |  Wyszynski, FJ., et al. 2010. Org Biomol Chem. 8: 4246-8. PMID: 20686715
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  9. Anhydrosaccharides-A new class of the fragile plastic crystals.  |  Kamińska, E., et al. 2018. J Chem Phys. 148: 074501. PMID: 29471664
  10. High-pressure dielectric studies on 1,6-anhydro-β-D-mannopyranose (plastic crystal) and 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose (canonical glass).  |  Heczko, D., et al. 2018. J Chem Phys. 148: 204510. PMID: 29865811
  11. Selective Microwave-Assisted Pyrolysis of Cellulose towards Levoglucosenone with Clay Catalysts.  |  Doroshenko, A., et al. 2019. ChemSusChem. 12: 5224-5227. PMID: 31693293
  12. Acid-catalyzed polymerization of 1,6-anhydro-β-D-glucopyranose  |   and Paul C. Wollwage, Paul A. Seib. 1971. Journal of Polymer Science. 9: 2877-2892.
  13. Synthesis of Hyperbranched Polysaccharide by Thermally Induced Cationic Polymerization of 1,6-Anhydrohexopyranose  |  Toshifumi Satoh, Tomoko Imai, Yoshikazu Kitajyo, Takahiro Maeda, Atsushi Narumi, Harumi Kaga, Noriaki Kaneko, Toyoji Kakuchi. 2004. Macromolecular Symposia. 217: 39-46.
  14. Synthesis, Branched Structure, and Solution Property of Hyperbranched d-Glucan and d-Galactan  |  Toshifumi Satoh, Tomoko Imai, Hiroyuki Ishihara, Takahiro Maeda, Yoshikazu Kitajyo, Yoko Sakai, Harumi Kaga, Noriaki Kaneko, Fumiaki Ishii, and Toyoji Kakuchi. 2005. Macromolecules. 38: 4202–4210.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

1,6-Anhydro-β-D-mannopyranose, 1 g

sc-220563
1 g
$340.00