60618-81-7

Usage

Chemical compound

A complex molecule derived from glucose.

Structure

Contains three acetyl groups and a benzylidene group attached to the sugar molecule.

Derivative of glucose

A modified form of the natural sugar, glucose.

Organic synthesis

Often used as a starting material for the preparation of various sugar derivatives.

Unique structure

Its specific arrangement of functional groups contributes to its utility in various applications.

Functional groups

Contains acetyl and benzylidene groups, which can participate in chemical reactions.

Applications in drug development

Useful in the development of new drugs due to its unique structure and functional groups.

Carbohydrate chemistry

Plays a role in the study of carbohydrate chemistry and biology.

Food industry

Has potential applications in the food industry for its sweetening properties.

Pharmaceutical industry

May have potential therapeutic effects and applications in the pharmaceutical industry.

Starting material

Serves as a precursor for the synthesis of other sugar derivatives.

Upstream product

• 30688-66-5 4,6-O-benzylidene-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 492-62-6 alpha-D-glucopyranose 

Downstream Products

• 17364-97-5 4,6-O-benzylidene-2,3-di-O-acetyl-α-D-glucopyranosyl fluoride 
• 182423-97-8 methyl 3-O-[4'-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-6'-O-benzoyl-2',3'-di-O-acetyl-α-D-glucopyranosyl]glycyrrhetinate 
• 182423-96-7 C₄₈H₆₆O₁₂ 

Relevant academic research and scientific papers

Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4-induced hepatic injury in vitro

Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively β-D-glucuronopyranosyl-(1→3)-β-D-glucopyranose, -(1→6)-α-D-glucopyranose, -(1→6)-β-D-glucopyranose, -(1→6)-β-D-galactopyranose, and β-D-galacturonopyranosyl-(→2)-β-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl β-D-glucuronopyranosyl-(1→4)-α-D-glucopyranosyl-D-glycyrrhe tinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and β-D-glucuronopyranosyl-(1→2)-β-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with β-D-glucuronopyranosylglucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal β-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal β-D-glucuronopyranose of 2 was replaced by β-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.

A new approach to some 1,6-dideoxy 1,6-epithio sugars

The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars.