New insights into the reactivity of 2-halo-glycals: Synthesis of novel iodinated O- and S-glycosides

Autor:	Agustín Ponzinibbio, Agustín H. Rojas, Virginia Vetere, Leticia Lafuente
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Sugar derivatives Ferrier rearrangement Anomer Chemistry Organic Chemistry Drug Discovery Thio Glycoside Reactivity (chemistry) Selectivity Biochemistry Combinatorial chemistry
Zdroj:	Tetrahedron Letters. 84:153459
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2021.153459
Popis:	We present the selective synthesis of new 2-iodo-2,3-unsaturated O- and S-glycosides. This is the first report on the Ferrier rearrangement of 2-halo-glycals with S-nucleophiles. We obtained α-glycosides in good yields and with high anomeric selectivity. We also describe the particular behavior of heteroaromatic thio sugar derivatives, where the C3 addition was performed in an alternative mechanism. We present a complete structure and conformation analysis by NMR.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d1de54dc191f70da0896bb776a4bdc58 https://doi.org/10.1016/j.tetlet.2021.153459 Zobrazit plný text záznamu Full Text from ScienceDirect