Ferrier Reaction: The first synthesis of 2,3-unsaturated seleno-glycosides by using alkyl(aryl) hydroselenides as the nucleophile and Hf(OTf)4 as the catalyst

Chen, Peiran; Ding, Yajun; Guo, Saisai; Zhang, Xiaoying

doi:10.1016/j.tetlet.2019.01.002

Cited by 6 publications

(2 citation statements)

References 30 publications

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“…For instance, treatment of glucal derivatives with organoselenolates, prepared in situ from diorganyl diselenides and catalytic amount hafnium(IV) triflate, gave 2,3-unsaturated organoselenyl glycosides 204 (Scheme 196). [277][278][279] The versatility of the diorganyl diselenides was also demonstrated in the synthesis of dibenzo selenophene derivatives 205 (Scheme 197). In this approach, the diorganyl diselenides, generated in situ from aryl diazonium salts, undergo a homolytic cleavage by the silver catalyst or visible light to form an arylselenyl radical.…”

Section: Miscellaneous Reactionsmentioning

confidence: 97%

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Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

do Carmo Pinheiro,

Souza Marques,

Ten Kathen Jung

et al. 2024

The Chemical Record

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Diorganyl diselenides have emerged as privileged structures because they are easy to prepare, have distinct reactivity, and have broad biological activity. They have also been used in the synthesis of natural products as an electrophile in the organoselenylation of aromatic systems and peptides, reductions of alkenes, and nucleophilic substitution. This review summarizes the advancements in methods for the transformations promoted by diorganyl diselenides in the main functions of organic chemistry. Parallel, it will also describe the main findings on pharmacology and toxicology of diorganyl diselenides, emphasizing anti‐inflammatory, hypoglycemic, chemotherapeutic, and antimicrobial activities. Therefore, an examination detailing the reactivity and biological characteristics of diorganyl diselenides provides valuable insights for academic researchers and industrial professionals.

show abstract

Section: Miscellaneous Reactionsmentioning

confidence: 97%

“…For instance, treatment of glucal derivatives with organoselenolates, prepared in situ from diorganyl diselenides and catalytic amount hafnium(IV) triflate, gave 2,3‐unsaturated organoselenyl glycosides 204 (Scheme 196). [277–279] …”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

do Carmo Pinheiro,

Souza Marques,

Ten Kathen Jung

et al. 2024

The Chemical Record

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Synthesis of Diverse Seleno‐Glycolipids via the Transacetalization of Selenoacetals

et al. 2021

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Seleno‐glycolipids, in which glycosidic oxygens are replaced with selenium atoms, are attractive detergents for X‐ray structural studies of membrane proteins. However, the development of seleno‐glycolipids has been hampered by difficulties associated with their chemical syntheses. In this study, we report a facile synthesis of novel seleno‐glycolipids with various glycan and lipid moieties, which proceeds via transacetalization of selenoacetals and glycosyl imidates. This work not only provides a route to monoseleno‐glycolipids, but also demonstrates the first synthesis of diseleno‐glycolipids.

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Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)4 and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

Chen

Guo

Zuo

et al. 2020

Tetrahedron Letters

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Ferrier Reaction: The first synthesis of 2,3-unsaturated seleno-glycosides by using alkyl(aryl) hydroselenides as the nucleophile and Hf(OTf)4 as the catalyst

Cited by 6 publications

References 30 publications

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

Synthesis of Diverse Seleno‐Glycolipids via the Transacetalization of Selenoacetals

Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)4 and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

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