154774-22-8

Upstream product

• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 30607-98-8 benzyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 58006-32-9 benzyl 4,6-O-benzylidene-β-D-glucopyranoside 

Downstream Products

• 154774-23-9 benzyl 2,3-O-bis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity

A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cel

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.

First and biomimetic total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A

The first total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A, was accomplished by relying on a biomimetic aldol-type formation of its characteristic C-aryl glucosidic bond through the exploitation of the inherent chemical reactivity of a glucopyranosic hemiacetal precursor.