70424-95-2

Basic information

• Product Name: 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-α-D-glucopyranose
• Synonyms: 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-α-D-glucopyranose
• CAS NO: 70424-95-2
• Molecular Weight: 2292.56
• Mol File: 70424-95-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-α-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-α-D-glucopyranose(70424-95-2)
• EPA Substance Registry System: 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-α-D-glucopyranose(70424-95-2)

Safety Data

• Hazardous Substances Data: 70424-95-2(Hazardous Substances Data)

Upstream product

• 492-62-6 alpha-D-glucopyranose 
• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 
• 492-61-5 β-D-glucose 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 

Downstream Products

• 14937-32-7 tannic acid 
• 70470-10-9 1,2,3,4,6-Penta-O-galloyl-alpha-D-glucopyranose 

Relevant articles and documents

Gallotannins and Tannic Acid: First Chemical Syntheses and in Vitro Inhibitory Activity on Alzheimer's Amyloid β-Peptide Aggregation

The screening of natural products in the search for new lead compounds against Alzheimer's disease has unveiled several plant polyphenols that are capable of inhibiting the formation of toxic β-amyloid fibrils. Gallic acid based gallotannins are among these polyphenols, but their antifibrillogenic activity has thus far been examined using "tannic acid", a commercial mixture of gallotannins and other galloylated glucopyranoses. The first total syntheses of two true gallotannins, a hexagalloylglucopyranose and a decagalloylated compound whose structure is commonly used to depict "tannic acid", are now described. These depsidic gallotannins and simpler galloylated glucose derivatives all inhibit amyloid β-peptide (Aβ) aggregation invitro, and monogalloylated α-glucogallin and a natural β-hexagalloylglucose are shown to be the strongest inhibitors.

Designing allosteric inhibitors of factor XIa. Lessons from the interactions of sulfated pentagalloylglucopyranosides

We recently introduced sulfated pentagalloylglucopyranoside (SPGG) as an allosteric inhibitor of factor XIa (FXIa) (Al-Horani et al., J. Med Chem. 2013, 56, 867-878). To better understand the SPGG-FXIa interaction, we utilized eight SPGG variants and a range of biochemical techniques. The results reveal that SPGG's sulfation level moderately affected FXIa inhibition potency and selectivity over thrombin and factor Xa. Variation in the anomeric configuration did not affect potency. Interestingly, zymogen factor XI bound SPGG with high affinity, suggesting its possible use as an antidote. Acrylamide quenching experiments suggested that SPGG induced significant conformational changes in the active site of FXIa. Inhibition studies in the presence of heparin showed marginal competition with highly sulfated SPGG variants but robust competition with less sulfated variants. Resolution of energetic contributions revealed that nonionic forces contribute nearly 87% of binding energy suggesting a strong possibility of specific interaction. Overall, the results indicate that SPGG may recognize more than one anion-binding, allosteric site on FXIa. An SPGG molecule containing approximately 10 sulfate groups on positions 2 through 6 of the pentagalloylglucopyranosyl scaffold may be the optimal FXIa inhibitor for further preclinical studies.

Anomeric selectivity in the synthesis of galloyl esters of d-glucose

The anomeric selectivity of the ester formation between d-glucopyranose and gallic acid was investigated under a variety of conditions. A new protocol was established that allows performing the reaction under conditions where mutarotation is very slow. Hi