154675-20-4

Basic information

• Product Name: dibenzyl 2,2',3,3',4,4'-hexabenzyloxybiphenyl-6,6'-dicarboxylate
• Synonyms: dibenzyl 2,2',3,3',4,4'-hexabenzyloxybiphenyl-6,6'-dicarboxylate
• CAS NO: 154675-20-4
• Molecular Weight: 1059.22
• Mol File: 154675-20-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dibenzyl 2,2',3,3',4,4'-hexabenzyloxybiphenyl-6,6'-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzyl 2,2',3,3',4,4'-hexabenzyloxybiphenyl-6,6'-dicarboxylate(154675-20-4)
• EPA Substance Registry System: dibenzyl 2,2',3,3',4,4'-hexabenzyloxybiphenyl-6,6'-dicarboxylate(154675-20-4)

Safety Data

• Hazardous Substances Data: 154675-20-4(Hazardous Substances Data)

Upstream product

• 103442-14-4 tetrabenzylellagic acid 
• 100-44-7 benzyl chloride 
• 476-66-4 ellagic acid 
• 915215-48-4 2,2'-dihydroxy-3,3,',4,4'-tetrakis(benzyloxy)-1,1'-biphenyl-6,6'-dicarboxylic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 193535-28-3 2,2',3,3',4,4'-hexabenzyloxydiphenyl-6,6'-dicarboxylic acid chloride 
• 154675-08-8 4,5,6,4',5',6'-Hexakis-benzyloxy-biphenyl-2,2'-dicarboxylic acid diethyl ester 
• 97152-19-7 dimethyl 4,4',5,5',6,6'-hexakis(benzyloxy)-[1,1'-biphenyl]-2,2'-dicarboxylate 
• 97152-40-4 2,2',3,3',4,4'-hexakis(benzyloxy)-1,1'-biphenyl-6,6'-dicarboxylic acid 

Relevant articles and documents

Synthetic studies toward c-glucosidic ellagitannins: A biomimetic total synthesis of 5-O-desgalloylepipunicacortein A

C-glucosidic ellagitannins constitute a subclass of bioactive polyphenolic natural products with strong antioxidant properties, as well as promising antitumoral and antiviral activities that are related to their capacity to interact with both functional and structural proteins. To date, most synthetic efforts toward ellagitannins have concerned glucopyranosic species. The development of a synthetic strategy to access C-glucosidic ellagitannins, whose characteristic structural feature includes an atropoisomeric hexahydroxydiphenoyl (HHDP) or a nonahydroxyterphenoyl (NHTP) unit that is linked to an open-chain glucose core by a C-aryl glucosidic bond, is described herein. The total synthesis of the biarylic HHDP-containing 5-O- desgalloylepipunicacortein A (1 β) was achieved by either using the natural ellagic acid bis-lactone as a precursor of the requested HHDP unit or by implementing an atroposelective intramolecular oxidative biarylic coupling to forge this HHDP unit. Both routes converged in the penultimate step of this synthesis to enable a biomimetic formation of the key C-aryl glucosidic bond in the title compound.

New hexahydroxybiphenyl derivatives as inhibitors of protein kinase C

We have previously shown that some ellagitannins are potent inhibitors of protein kinase C (PKC). On the basis of this finding, several series of hexahydroxybiphenyl derivatives of ellagic acid were synthesized as simple analogs of these ellagitannins and were evaluated for their inhibitory effect against PKC. Compounds 23 and 26 were found to be potent inhibitors of PKC, while hexakis(benzyloxy)biphenyl derivatives exhibited weak anti-PKC activity.