19949-47-4

Usage

Uses

Used in Pharmaceutical Industry:
Neohesperidose heptaacetate is used as a synthetic building block for the preparation of flavonol glycosides, which are known for their immunosuppressant properties. These flavonol glycosides are isolated from the leaves of Boscia salicifolia Oliv and have potential applications in the development of new drugs for various immune-related disorders.
Used in Chemical Synthesis:
As a disaccharide, neohesperidose heptaacetate is utilized in the chemical synthesis of various compounds, particularly those with potential pharmaceutical or biological applications. Its unique structure and functional groups make it a versatile starting material for the development of novel molecules with specific properties and functions.

Upstream product

• 10236-47-2 naringin 
• 108-24-7 acetic anhydride 
• 2781-65-9 2-O-α-L-rhamnopyranosyl-D-galactopyranose 

Relevant academic research and scientific papers

A straightforward access to neohesperidose from naringin by acetolysis. Comparative behaviour of some flavonoid neohesperidosides and rutinosides under acetolysis

A straightforward semisynthesis of neohesperidose was performed in three-steps with 43% overall yield starting from naringin, the main flavonoid of grapefruit. In addition, the behaviour of two pairs of flavonoid 7-O-rhamnoglucosides (neohesperidosides naringin and rhoifolin; rutinosides hesperidin and diosmin) under same acetolysis conditions was compared. Results demonstrated the crucial influence of the oxidation state of the aglycone (flavanone or flavone), and of the nature of the disaccharidic moiety on the course of the reaction.

SYNTHESIS OF 2-O-α, 3-O-α, 3-O-β, AND 4-O-α-L-RHAMNOPYRANOSYL-D-GALACTOSE

Condensation of benzyl 3-O-benzoyl-4,6-O-benzylidene-, benzyl 2-O-benzoyl-4,6-O-benzylidene- (2), and benzyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside, separately, with tri-O-acetyl-α-L-rhamnopyranosyl bromide gave mainly α-linked disaccharide derivatives.An appreciable proportion of the β-linked disaccharide was also abtained from 2.An anomalous deacylation reaction was found for the (1-->3)-linked disaccharide, and the partially benzoylated products were isolated and characterised.The anomeric configuration of each disaccharide was established on the basis of JC-1,H-1 values.The chemical shifts for the galactose moieties of the α and β-L-rhamnopyranosyl derivatives differed in a systematic way.