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2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose (CAS 14131-84-1)

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Alternate Names:
D-Mannose diacetonide
CAS Number:
14131-84-1
Purity:
≥98%
Molecular Weight:
260.29
Molecular Formula:
C12H20O6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose is a key compound in carbohydrate chemistry research, serving as a building block for the synthesis of various carbohydrate derivatives and mimetics. Its mechanism of action is rooted in its chemical structure, featuring isopropylidene groups protecting the 2,3 and 5,6 hydroxyl positions of the mannofuranose ring. This protective strategy enhances the stability of the compound and allows for selective functionalization at other hydroxyl groups. Researchers utilize 2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose in the synthesis of complex carbohydrate structures, including glycosides, glycoconjugates, and oligosaccharides. By employing chemical transformations such as glycosylation, glycosidation, and glycosyl transfer reactions, scientists can access diverse glycan motifs for studying carbohydrate-protein interactions, cell recognition processes, and carbohydrate-mediated signaling pathways. Additionally, this compound serves as a precursor for the preparation of carbohydrate-based materials and biomimetic systems with applications in biotechnology, materials science, and drug delivery. Its compatibility with various synthetic methodologies and ease of manipulation make it a valuable tool for elucidating the roles of carbohydrates in biological systems and developing carbohydrate-based diagnostics. Through its versatile applications in carbohydrate research, 2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose contributes to advancements in understanding carbohydrate structure-function relationships and exploiting their potential in diverse research fields.


2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose (CAS 14131-84-1) References

  1. Preparation and evaluation of the in vitro erythroid differentiation induction properties of some esters of methyl 3,4-O-isopropylidene-beta-D-galactopyranoside and 2,3-O-isopropylidene-D-mannofuranose.  |  Catelani, G., et al. 2002. Bioorg Med Chem. 10: 347-53. PMID: 11741783
  2. An improved synthesis of a key intermediate for (+)-biotin from D-mannose.  |  Chen, FE., et al. 2007. Carbohydr Res. 342: 2461-4. PMID: 17678881
  3. Zeolite catalyzed selective deprotection of di- and tri-O-isopropylidene sugar acetals.  |  Bhaskar, PM., et al. 2008. Carbohydr Res. 343: 1801-7. PMID: 18502410
  4. A novel synthetic approach to C-glycosyl-D- and L-alanines.  |  Martinková, M., et al. 2008. Molecules. 13: 3171-83. PMID: 19078857
  5. 2,3;5,6-Di-O-isopropyl-idene-1-O-(2-phenyl-acet-yl)-α-d-mannofuran-ose.  |  Sacui, IA., et al. 2010. Acta Crystallogr Sect E Struct Rep Online. 66: o2341. PMID: 21588686
  6. Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides.  |  Yu, H., et al. 2011. Bioorg Med Chem Lett. 21: 5037-40. PMID: 21592790
  7. An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors.  |  Ghosh, AK., et al. 1991. J Org Chem. 56: 6500-6503. PMID: 30393394
  8. Recent progress in chemical synthesis of bacterial surface glycans.  |  Li, R., et al. 2020. Curr Opin Chem Biol. 58: 121-136. PMID: 32920523
  9. The Bucherer-Bergs Multicomponent Synthesis of Hydantoins-Excellence in Simplicity.  |  Kalník, M., et al. 2021. Molecules. 26: PMID: 34209381
  10. Synthesis and biological activities of petrosiols B and D.  |  Geng, J., et al. 2019. RSC Adv. 9: 10253-10263. PMID: 35520890

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose, 5 g

sc-220790
5 g
$91.00