34546-55-9Relevant academic research and scientific papers
Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor
Tiwari, Varsha,Badavath, Vishnu Nayak,Singh, Adesh Kumar,Kandasamy, Jeyakumar
, p. 227 - 236 (2020/03/18)
Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.
Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence
Ayers, Benjamin J.,Hollinshead, Jacqueline,Saville, Alexander W.,Nakagawa, Shinpei,Adachi, Isao,Kato, Atsushi,Izumori, Ken,Bartholomew, Barbara,Fleet, George W.J.,Nash, Robert J.
, p. 126 - 131 (2014/03/21)
Iteamine, o-aminobenzyl β-d-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of d-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver α-N-acetylgalactosaminidase.
Synthetic studies toward c-glucosidic ellagitannins: A biomimetic total synthesis of 5-O-desgalloylepipunicacortein A
Malik, Ga?lle,Natangelo, Anna,Charris, Jaime,Pouységu, Laurent,Manfredini, Stefano,Cavagnat, Dominique,Buffeteau, Thierry,Deffieux, Denis,Quideau, Stéphane
supporting information; experimental part, p. 9063 - 9074 (2012/10/07)
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.
