Switchable synthesis of glycosyl selenides or diselenides with direct use of selenium as the selenating agent

Autor:	Emiliano Bedini, Serena Traboni, Domenica Capasso, Giulia Vessella, Alfonso Iadonisi, Sonia Di Gaetano, Sabrina Cuomo
Přispěvatelé:	Iadonisi, A., Traboni, S., Capasso, D., Bedini, E., Cuomo, S., Di Gaetano, S., Vessella, G.
Rok vydání:	2021
Předmět:	Diselenide Sodium borohydride chemistry.chemical_compound chemistry Selenide Organic Chemistry Halide chemistry.chemical_element Glycosyl Chemoselectivity Combinatorial chemistry Selenium Stoichiometry
Zdroj:	Organic Chemistry Frontiers. 8:1823-1829
ISSN:	2052-4129
DOI:	10.1039/d1qo00045d
Popis:	Symmetrical diglycosyl-selenides or diselenides can be readily prepared with high chemoselectivity by direct use of elementary selenium as a cheap selenating agent (reduced in situ by sodium borohydride), and glycosyl iodides (or other halides) as reactive glycosyl donors. The chemoselectivity of the synthesis is critically affected by both the presence or not of triethyl phosphite, and the sodium borohydride to selenium stoichiometric ratio. Taking advantage of indications from mechanistic studies, the scope of the strategy was further extended to the synthesis of unsymmetrical diglycosyl selenides. Preliminary biological experiments evidenced an interesting antiproliferative effect of galactosyl diselenide against some tumor cell lines, otherwise negligible with the corresponding selenide.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0a97f8f85606463e9a04d4765a53122f https://doi.org/10.1039/d1qo00045d Zobrazit plný text záznamu