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2,3:5,6-Di-O-isopropylidene-L-gulonolactone (CAS 7306-64-1)

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Application:
2,3:5,6-Di-O-isopropylidene-L-gulonolactone is a useful synthetic intermediate for carbohydrate synthesis
CAS Number:
7306-64-1
Molecular Weight:
258.27
Molecular Formula:
C12H18O6
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-L-gulonolactone, a derivative of L-gulonolactone, plays a crucial role in various research applications, particularly in the synthesis of carbohydrate-based compounds and the study of carbohydrate chemistry. Its unique structure, featuring two isopropylidene groups attached to the hydroxyl groups at positions 2, 3, 5, and 6 of the gulonolactone ring, provides stability and protection to the reactive hydroxyl moieties, making it a versatile building block for the synthesis of complex carbohydrates and glycoconjugates. Researchers have utilized this compound as a precursor in the synthesis of various carbohydrate derivatives, such as glycosides, glycosylamines, and glycosyl esters, through selective deprotection and functional group manipulation strategies. Additionally, 2,3:5,6-Di-O-isopropylidene-L-gulonolactone has been employed in the study of carbohydrate metabolism and enzymology, serving as a substrate for enzymes involved in glycoside hydrolysis, glycosyl transfer reactions, and carbohydrate modification processes. Furthermore, its use as a protecting group in carbohydrate synthesis enables the selective manipulation of specific hydroxyl groups, facilitating the controlled construction of oligosaccharides and glycoconjugates with desired structures and properties. Overall, 2,3:5,6-Di-O-isopropylidene-L-gulonolactone remains an indispensable tool in carbohydrate research, enabling the synthesis of diverse carbohydrate-based molecules and advancing our understanding of carbohydrate biochemistry and biology.


2,3:5,6-Di-O-isopropylidene-L-gulonolactone (CAS 7306-64-1) References

  1. Synthesis and evaluation of isourea-type glycomimetics related to the indolizidine and trehazolin glycosidase inhibitor families.  |  García-Moreno, MI., et al. 2003. J Org Chem. 68: 8890-901. PMID: 14604359
  2. Concise synthesis of orthogonally diprotected l-glyceraldehyde  |  Estefanía Dibello, Margarita Brovetto, Gustavo Seoane, Daniela Gamenara. 2013. Tetrahedron Letters. 54: 5895-5897.
  3. High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues  |  Maxime Moreaux, Guillaume Bonneau, Aurélien Peru, Fanny Brunissen, Marine Janvier, Arnaud Haudrechy, Florent Allais. 2019. European Journal of Organic Chemistry. 2019: 1600-1604.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2,3:5,6-Di-O-isopropylidene-L-gulonolactone, 5 g

sc-220791
5 g
$280.00