Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction

Mariola Koszytkowska-Stawińska , Wojciech Sas

Abstract

Nucleoside analogs with the 4,5-dimethyl-NH-1,2,3-triazolo-linker between thymine and a carbohydrate, or a hydroxyalkoxyl, or phosphonomethoxyl residue, were obtained by the Bannert cascade reaction from 1-(4-azidobut-2-yn-1-yl)thymine and the carbohydrate or acyclic alcohol. The reaction conditions were developed on the basis of a thermal analysis of the starting azide and by the optimization of the reaction components ratio. The best results were obtained when the reaction cascade employed the azide/nucleophile molar ratio of 1/14, at 55 °C, with no solvent addition. The reaction showed good discrimination between the pentofuranose hydroxyls, yielding triazoles linked at the carbohydrate 5′-oxygen atom.
Author Mariola Koszytkowska-Stawińska (FC / DOC)
Mariola Koszytkowska-Stawińska,,
- Department Of Organic Chemistry
, Wojciech Sas (FC / DOC)
Wojciech Sas,,
- Department Of Organic Chemistry
Journal seriesTetrahedron, ISSN 0040-4020
Issue year2013
Vol69
No12
Pages2619-2627
Publication size in sheets0.5
Keywords in Englishnucleoside analogs, fleximers, NH-1,2,3-Triazoles, propargyl azides, Banert cascade reaction
ASJC Classification1605 Organic Chemistry; 3002 Drug Discovery; 1303 Biochemistry
DOIDOI:10.1016/j.tet.2013.01.042
URL http://www.sciencedirect.com/science/article/pii/S0040402013001038
Languageen angielski
File
tetrahedron_2013_69_2619.pdf 729.84 KB
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 01-01-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 01-01-2020, ArticleFromJournal
Publication indicators Scopus Citations = 11; WoS Citations = 9; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 0.905; WoS Impact Factor: 2013 = 2.817 (2) - 2013=2.772 (5)
Citation count*2 (2015-05-22)
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