Pu 2086 plus intelligent prep pump

One-dimensional and two-dimensional NMR spectra were acquired on an AVANCE III (400 MHz) (Bruker BioSpin, Rheinstetten, Germany), with chemical shifts expressed in ppm. The NMR spectra were referenced to residual solvent peaks (CD₃OD: ¹H NMR 3.30 ppm, ¹³C NMR 49.0 ppm). HR-ESI-MS spectra were acquired on a Thermo Fisher Scientific Q-Exactive HR-ESI-Orbitrap-MS (Waltham, MA, USA). Medium pressure liquid chromatography (MPLC) was conducted using an AI-580 system equipped with an ULTRA PAK ODS-SM-50D (50 µm, 50 × 300 mm, Yamazen Corporation, Osaka, Japan). Reversed-phase (RP)-HPLC separations were performed with a recycling system comprising a PU-2086 Plus Intelligent prep pump (Jasco, Tokyo, Japan), UV-2075 detector (Jasco, Tokyo, Japan), Capcell Pak UG120 C18 column (5 μm, 20 × 250 mm, Osaka Soda, Osaka, Japan), Capcell Pak UG120 C18 column (5 μm, 10 × 250 mm, Osaka Soda, Osaka, Japan), and HPLC-grade solvents. For analytical HPLC, a PU-4180 RHPLC pump (Jasco, Tokyo, Japan), MD-4017 photodiode array detector (Jasco, Tokyo, Japan), and AS-4050 HPLC autosampler (Jasco, Tokyo, Japan) were used. Data were analysed using ChromNAV software v.2 (Jasco, Tokyo, Japan).

One-dimensional (¹H and ¹³C) and two-dimensional NMR spectra were measured on a Bruker AVANCE III 400 instrument (Bruker BioSpin, Billerica, MA, USA). Chemical shifts (δ) were reported in parts per million and coupling constants (J) were reported in hertz. The chemical shifts in the ¹H and ¹³C NMR spectra were corrected using the residual solvent signals. HR-ESIMS was performed using an Accela LC system (Thermo Fisher Scientific, Waltham, MA, USA) equipped with a quadrupole mass spectrometer (Q-Exactive; Thermo Fisher Scientific). RP-HPLC analyses were conducted using a PU-2086 Plus intelligent prep pump (Jasco Co., Inc., Tokyo, Japan) with the UV-970 UV/VIS detector (Jasco Co., Inc.), a Shiseido Capcell Pak C18 UG120 (4.6 × 250 mm) column for analysis, and a Shiseido Capcell Pak C18 U120 (20 × 250 mm) column for preparative purposes. Preparative normal-phase HPLC was performed using the same pump and detector with a Nomura Chemical (Aichi, Japan) Develosil 60-5 (7.5 × 250 mm) column.