400 anova advance

¹H and ¹³C NMR spectra were recorded at 500/125 MHz on a Bruker 500 AVANCE NEO spectrometer (Karlsruhe, Germany) or at 400/100 MHz on a Bruker 400 Anova Advance. The spectra were recorded using CDCl₃ or (CD₃)₂CO, and the same solvents were used as internal standards. Electrospray ionization mass spectra (ESIMS) were performed using the LC/MS TOF system AGILENT 6230B (Agilent Technologies, Milan, Italy), HPLC 1260 Infinity. Column chromatography (CC) was performed using silica gel (Kieselgel 60, 0.063–0.200 mm, Merck, Darmstadt, Germany). Thin-layer chromatography (TLC) was performed on analytical and preparative silica gel plates (Kieselgel 60, F₂₅₄, 0.25 and 0.5 mm, respectively, Merck, Darmstadt, Germany). The spots were visualized via exposure to UV light (254 nm) and/or iodine vapours and/or by spraying first with 10% H₂SO₄ in MeOH and then with 5% phosphomolybdic acid in EtOH, followed by heating at 110 °C for 10 min. Sigma-Aldrich Co. (St. Louis, MO, USA) supplied all the reagents and the solvents.

A Bruker 400 Anova Advance (Karlsruhe, Germany) spectrometer was used to record the proton nuclear magnetic resonance (¹H NMR) at 400 MHz. CDCl₃ was used as a solvent and internal standard. A digital polarimeter, the JASCO P-1010 (Tokyo, Japan), was used to measure the optical rotations. Liquid Chromatography/Mass Spectrometry-Time of Flight (LC/MS TOF) system AGILENT 6230B (Agilent Technologies, Milan, Italy) and High-performance liquid chromatography (HPLC) 1260 Infinity were used to perform Electrospray ionisation mass spectra (ESIMS). Column chromatography (CC) was performed using silica gel (Kieselgel 60, 0.063–0.200 mm, Merck, Darmstadt, Germany). Analytical and preparative silica gel plates (Kieselgel 60, F₂₅₄, 0.25 and 0.5 mm, respectively, Merck, Darmstadt, Germany) and thin-layer chromatography (TLC) were performed. Spots Visualization was carried out by exposure to UV light (254 nm) and/or iodine vapors and/or by spraying first with 10% H₂SO₄ in MeOH and then with 5% phosphomolybdic acid in EtOH, followed by heating at 110 °C for 10 min. Sigma-Aldrich Co. (St. Louis, MO, USA) supplied all the reagents and the solvents.

Electrospray ionization mass spectrometry (ESI MS) and liquid chromatography/mass spectrometry (LC/MS) analyses were performed using an LC/MS TOF system Agilent 6230B (Agilent Technologies, Milan, Italy), HPLC 1260 Infinity. A Phenomenex (Bologna, Italy) Luna (C18 (2) 5 mm, 150–4.6 mm column) was used to perform the high-performance liquid chromatography (HPLC) separations. Bruker 400 Anova Advance (Karlsruhe, Germany) was used to record the ¹H NMR spectra at 400 MHz in CDCl₃ at 298 K. Analytical, preparative, and reverse-phase thin-layer chromatography (TLC) were carried out on silica gel (Merck, Kieselgel 60, F₂₅₄, 0.25, 0.5 mm, and RP-18 F_254s, respectively) plates (Merck, Darmstadt, Germany). The spots were visualized as previously described [20 (link)]. Column chromatography (CC) was performed using silica gel (Kieselgel 60, 0.063–0.200 mm) and C₁₈-reversed phase silica gel (230–400 mesh) (Merck, Darmstadt, Germany). Sigma-Aldrich Co. (St. Louis, MO, USA) supplied all the reagents and the solvents.