Studies on epimeric D-xylo-and D-lyxo-tetritol-1-yl-2-phenyl-2H-1,2,3-triazoles. Synthesis and anomeric configuration of 4-(alpha- and beta-D-threofuranosyl)-2-phenyl-2H-1,2,3-triazole C-nucleoside analogs
Mae. Sallam et al., Studies on epimeric D-xylo-and D-lyxo-tetritol-1-yl-2-phenyl-2H-1,2,3-triazoles. Synthesis and anomeric configuration of 4-(alpha- and beta-D-threofuranosyl)-2-phenyl-2H-1,2,3-triazole C-nucleoside analogs, NUCLEOS NUC, 19(5-6), 2000, pp. 941-954
Treatment of 4-(D-xylo-tetritol-1-yl-2-phenyl-2H-1,2,3-triazole (1) with on
e mole equivalent of tosyl chloride in pyridine solution, afforded the C-nu
cleoside analog; 4-(beta-D-threofuranosyl)-2-phenyl-2H-1,2,3-triazole (2) i
n 55% yield as well as the byproduct 4-(4-chloro-4-deoxy-D-xylo-tetritol-1-
yl)-2-phenyl-2H-1,2,3-triazole (4). Treatment of the epimeric 4-(D-lyxo-tet
ritol-1-yl)-2-phenyl-2H-1,2,3-triazole (6) with tosyl chloride in pyridine
solution afforded the anomeric C-nucleoside analog;4-(alpha-D-threofuranosy
l)-2-phenyl-2H-1,2,3-triazole (7) in 29% yield, as well as the byproduct 4-
(4-chloro-4-deoxy-D-lyxo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazole (9). Sim
ilar treatment of 1 and 6 with trifluoromethanesulfonyl chloride in pyridin
e solution afforded 2 and 7, respectively. The structure and anomeric confi
guration of these compounds were determined by acetylation, NMR, NOE, and c
ircular dichroism spectroscopy, as well as mass spectrometry.