The author of 《Triazolyl C-nucleosides via the intermediacy of β-1′-ethynyl-2′-deoxyribose derived from a Nicholas reaction: Synthesis, photophysical properties and interaction with BSA》 were Bag, Subhendu Sekhar; Das, Suman Kalyan. And the article was published in Tetrahedron in 2019. Synthetic Route of C30H30N10 The author mentioned the following in the article:
We report the design and synthesis of triazolyl donor/acceptor unnatural C-nucleosides via alkyne (sugar)-azide (aromatic) 1, 3-dipolar cycloaddition reaction as a key step and studies on their photophys. properties. We have chosen β-1′-ethynyl-2′-deoxyribose as a precursor to synthesize triazolyl-C-nucleosides. Overcoming the difficulties, we obtain β-1′-ethynyl-2′-deoxyribose as a major product following a Co2(CO)8 catalyzed intramol. Nicholas reaction. The 1,3-diaxial interaction is the driving force for the α to β-anomeric conversion while performing cobalt complexation followed by oxidation to afford β-1′- ethynyl-2′-deoxyribose as the major product. A Cu(I)-catalyzed click reaction between different aromatic donor/acceptor azides and β-1′- ethynyl-2′-deoxyribose generates the desired unnatural triazolyl donor-acceptor aromatic C-nucleosides (cTBDo/Ac) within 30 min. Single crystal X-ray structure shows the puckered conformation of sugar as C3′-exo. Studies on the photophys. properties suggests good fluorophoric as well as solvatochromic characteristics of these nucleosides. Two of the synthesized nucleosides, cTAnthBDo and cTPyBDo, are found to interact with BSA as the only tested protein with quenching of fluorescence signal. The designed bases, thus, might find applications in stabilizing a DNA and in the biophys. study thereof, if a pair of such donor acceptor C-nucleosides could be incorporated into a DNA sequence. After reading the article, we found that the author used Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8Synthetic Route of C30H30N10)
Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8) can stabilizes Cu(I) towards disproportionation and oxidation thus enhancing its catalytic effect in the azide-acetylene cycloaddition.Synthetic Route of C30H30N10
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics