Atomfair

Awaiting product image

Atomfair 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose C19H26O6

Description 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (CAS No. 22331-21-1) is a highly specialized carbohydrate derivative extensively utilized in synthetic organic chemistry and glycoscience research. This compound, with the molecular formula C19H26O6, features a benzyl-protected hydroxyl group at the 3-position and isopropylidene acetal protections at the 1,2- and 5,6-positions of the D-glucofuranose scaffold. Its IUPAC name is 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole . This compound serves as a pivotal intermediate in the synthesis of complex oligosaccharides, glycoconjugates, and other bioactive molecules. The benzyl and isopropylidene protecting groups enhance its stability and reactivity, making it ideal for selective glycosylation reactions. It is supplied as a high-purity solid (>98%) with rigorous…

Category:
Brands:

Description

Description

3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose (CAS No. 22331-21-1) is a highly specialized carbohydrate derivative extensively utilized in synthetic organic chemistry and glycoscience research. This compound, with the molecular formula C19H26O6, features a benzyl-protected hydroxyl group at the 3-position and isopropylidene acetal protections at the 1,2- and 5,6-positions of the D-glucofuranose scaffold. Its IUPAC name is 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole.

This compound serves as a pivotal intermediate in the synthesis of complex oligosaccharides, glycoconjugates, and other bioactive molecules. The benzyl and isopropylidene protecting groups enhance its stability and reactivity, making it ideal for selective glycosylation reactions. It is supplied as a high-purity solid (>98%) with rigorous QC validation via NMR, HPLC, and MS to ensure consistency for sensitive applications.

Synonyms include NSC 56267 and BRN 0043822. Store under inert conditions at 2-8??C to maintain stability.

  • CAS No: 22331-21-1
  • Molecular Formula: C19H26O6
  • Molecular Weight: 350.4
  • Exact Mass: 350.17293854
  • Monoisotopic Mass: 350.17293854
  • IUPAC Name: 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  • SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)OCC4=CC=CC=C4)C
  • Synonyms: 18685-18-2, 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole, NSC 56267, BRN 0043822

Application

3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose is widely employed as a key building block in carbohydrate chemistry for the stereoselective synthesis of glycosides and nucleosides. Its protected hydroxyl groups enable controlled deprotection strategies, facilitating the construction of structurally diverse glycans. Researchers also utilize it in the development of glycomimetics and enzyme inhibitors targeting glycosidases. This compound is particularly valuable in medicinal chemistry for probing sugar-protein interactions.

If you are interested or have any questions, please contact us at support@atomfair.com