Studies on the dehydrative cyclization of epimeric 4‐(L‐xylo and L‐lyxo‐tetritol‐1‐yl)‐2‐phenyl‐2H‐1,2,3‐triazoles. Circular dichroism and NMR assignment of the formed anomeric C‐nucleoside L‐threofuranosyl triazole analogs

Abstract

Dehydrative cyclization of epimeric 4-(L-xylo- and L-lyxo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazoles afforded the anomeric alpha and beta-L-threofuranosyl analogs. The anomeric configuration of the formed anomeric C-nucleoside analogs was determined by circular dichroism and NMR spectroscopy.

Circular dichroism as a reliable tool for anomeric assignment of glycosyl‐2‐phenyl‐2H‐1,2,3‐triazole C‐nucleoside analogs. A rule for prediction of their anomeric configuration

“…The anomeric configuration of compounds 11-13 could not be obtained readily from their 17 The NOE difference for 11 ( former of an a-D-arabinopyranosyl ring for 14. These NOE results for 11-14 supports the chiroptical CD assignment for compounds 7-10, and supports the CD rule for predicting the anomeric configuration of 4-glycosyl-2-phenyl-2H-1,2,3-triazole C-nucleoside analogs, in general.…”

Chiroptical Assignment of the Anomeric Configuration of 4-(α,β-D-lyxopyranosyl)- and 4-(α,β-D-lyxofuranosyl)-2-phenyl-2H-1,2,3-Triazole C-Nucleoside Anomeric Pairs: Extension of the CD Triazole Rule

“…In addition, the CD triazole rule is applicable for acyclic polyhydroxyalkyl-2-phenyl-2H-1,2,3-triazole analogs, supporting the El-Khadem triazole rule for specific rotation at the D-line. It is also applicable for C-nucleosides having different cyclic glycosyl parts: D-glycopyranosyl, [1] D-glycofuranosyl, [18] 5 -hydroxymethyl-D-glycofuranosyl, [1] and L-glycofuranosyl [19] analogs. …”