Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases
摘要:
The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside la bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherification or a Friedel-Crafts glycosylation as key steps. The synthesis of the triazolyl derivative 1b was achieved using a convergent 1,3-dipolar cycloaddition strategy. Fluorescence studies show that 3-HC-thienyl-nucleoside la displays high sensitivity of its dual emission to polarity changes and therefore is highly promising for nucleic acid labelling. (C) 2009 Elsevier Ltd. All rights reserved.
Efficient Synthesis of α- and β-2′-Deoxy-heteroaryl-<i>C</i>-nucleosides
作者:Alain Burger、Rachid Benhida、Marie Spadafora
DOI:10.1055/s-2008-1072589
日期:2008.5
A short and efficient method for the synthesis of a series of 2′-deoxy-heteroaryl- C-nucleosides has been developed by the application of aryl-aldol condensation followed by P-toluenesulfonic acid (PTSA)-mediated isopropylidene cleavage and subsequent cycloetherification.