Triazole-fused sugars from nitroalkene-containing C-glycosides by a tandem 1,3-dipolar cycloaddition and intramolecular Michael addition

Unusual Effect of Impurities on the Spectral Characterization of 1,2,3-Triazoles Synthesized by the Cu-Catalyzed Azide–Alkyne Click Reaction

“…NMR spectroscopy is currently one of the most convenient, widely used, and actively developing methods for determining the structure of organic molecules. − The disappearance of individual signals in well-resolved spectra without other visible distortions is a rare phenomenon that cannot be easily identified. For example, cases of “signal disappearance” in the 15 N NMR spectrum due to deprotonation of the amide fragment in the peptide by transition metal ions, as well as the disappearance of two signals in the 13 C spectrum of 1-unsubstituted 1,2,3-triazole due to tautomerism, have been described previously . Incomplete NMR spectra of 1-substituted 1,2,3-triazoles obtained by the click reaction of copper­(I)-catalyzed azide–alkyne cycloaddition were also published, but this effect was not commented upon (see refs − and their corresponding Supporting Information).…”

“…For example, cases of "signal disappearance" in the 15 N NMR spectrum due to deprotonation of the amide fragment in the peptide by transition metal ions, 33 as well as the disappearance of two signals in the 13 C spectrum of 1unsubstituted 1,2,3-triazole due to tautomerism, have been described previously. 34 Incomplete NMR spectra of 1substituted 1,2,3-triazoles obtained by the click reaction of copper(I)-catalyzed azide−alkyne cycloaddition were also published, but this effect was not commented upon (see refs 35−38 and their corresponding Supporting Information). This is a quite challenging case, which was either not explained or overlap with other signals was assumed.…”

Enantioselective synthesis of (−)-paeonilide

“…The actual experiment, using 187 as starting material, was carried out following the procedure of Zou et al, who used this methodology for the oxidation of an allyl group connected to carbohydrate derivatives. 133,136 Already the first tests showed a cleaner reaction compared to the Wacker-oxidations applied before (Table 12, entry 3). There was also no problem during the isolation of the product concerning solvent residues after column chromatography, as occurred when using DMF or DMA, respectively.…”

Synthesis of (4S)‐4‐C‐spiro‐glycosyl‐chromeno‐[3,4‐d][1,2,3]triazoles: Biological evaluation and molecular docking investigation

“…In addition, these moieties find wide range of applications in industries such as photo‐sensitizers, dyes, agrochemicals, and commercially employed as anti‐corrosive agents (Figure 1). [ 1–9 ]…”

“…In addition, these moieties find wide range of applications in industries such as photo-sensitizers, dyes, agrochemicals, and commercially employed as anti-corrosive agents (Figure 1). [1][2][3][4][5][6][7][8][9] Not only 1,2,3 triazoles but also "C-glycosides are an important class of compounds resistant to metabolic processes. [10] C-glycosides are used in synthesis of enzyme inhibitors and drug molecules for certain viral diseases such as HIV, hepatitis B and herpes virus.…”