18402-97-6Relevant articles and documents
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Schreier et al.
, p. 35,39 (1954)
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Studies on epimeric-D-arabino- and -D-ribo-tetritol-1-yl-2-phenyl-2 h- 1,2,3-triazoles. Synthesis and anomeric configuration of 4-(α- and β-D- erythrofuranosyl)-2-phenyl-2 h-1,2,3-triazole C-nucleoside analogs
Sallam, Mohammed A. E.,Louis, Farida F.,Cassady, John M.
, p. 769 - 783 (2007/10/03)
Treatment of 4-(D-arabino-tetritol-l-yl)-2-phenyl-2 H-1,2,3-triazole (1) with one mole equivalent of tosyl chloride in pyridine solution, afforded the C-nucleoside analogs, 4-(α-D-erythrofuranosyl)-2-phenyl-2 H- 1,2,3-triazole (2) in 25% yield, as well as the byproduct 4-(4-chloro-4-deoxy-D-arabino- tetritol-l-yl)-2-phenyl-2 H-1,2,3-triazole(3). Treatment of the epimeric 4- (D-ribo-tetritol-l-yl)-2-phenyl-2 H-1,2,3-triazole(8) with tosyl chloride in pyridine solution afforded the anomeric C-nucleoside analogs, 4-(β-D- erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (9) in 23% yield. Similar treatment of 8 with trifluoromethanesulfonyl chloride in pyridine solution afforded 9. The structure and anomeric configuration of these compounds were determined by acylation, NMR, NOE, circular dichroism spectroscopy and mass spectrometry.