Aglient 1200 lc msd trap spectrometer

Optical rotations were determined using a Jasco DIP-370 automatic polarimeter (Jasco, Tokyo, Japan Manufacturer, City, State if USA/Canada, Country). The NMR spectra were recorded using a BRUKER AVANCE III 600 (¹H, 600 MHz; ¹³C, 150 MHz) (Bruker Biospin GmbH, Karlsruhe, Germany), with tetramethylsilane (TMS) as an internal standard. Heteronuclear multiple quantum correlation (HMQC), heteronuclear multiple bond correlation (HMBC), rotating frame nuclear overhauser effect spectroscopy (ROESY), and ¹H–¹H correlation spectroscopy (COSY) spectra were recorded using a pulsed field gradient. The HR-ESI-MS spectra were obtained by using an Aglient 1200 LC-MSD Trap spectrometer (Agilent, Santa Clara, CA, USA). Preparative HPLC was performed using a GILSON 321 pump, 151 UV/VIS detector (Gilson, VILLIERS-LE-BEL, France), and RStech HECTOR-M C₁₈ column (5-micron, 250 × 21.2 mm) (RS Tech Crop, Chungju, South Korea). Column chromatography was performed using a silica gel (Kieselgel 60, 70–230, and 230–400 mesh, Merck, Darmstadt, Germany), YMC C-18 resins, and thin layer chromatography (TLC) was performed using pre-coated silica-gel 60 F₂₅₄ and RP-18 F_254S plates (both 0.25 mm, Merck, Darmstadt, Germany), the spots were detected under UV light and using 10% H₂SO₄.

Optical rotations were determined using a Jasco DIP-370 automatic polarimeter (Jasco, Tokyo, Japan). The NMR spectra were recorded using a BRUKER AVANCE III 600 (¹H, 600 MHz; ¹³C, 150 MHz) (Bruker Biospin GmbH, Karlsruhe, Germany), with tetramethylsilane (TMS) as an internal standard. Heteronuclear multiple quantum correlation (HMQC), heteronuclear multiple bond correlation (HMBC), rotating frame nuclear overhauser effect spectroscopy (ROESY), and ¹H–¹H correlation spectroscopy (COSY) spectra were recorded using a pulsed field gradient. The HR-ESI-MS spectra were obtained by using an Aglient 1200 LC-MSD Trap spectrometer (Agilent, Santa Clara, CA, USA). Preparative HPLC was performed using a GILSON 321 pump, 151 UV–VIS detector (Gilson, VILLIERS-LE-BEL, France), and RStech HECTOR-M C₁₈ column (5-micron, 250 × 21.2 mm) (RS Tech Crop, Chungju, South Korea). Column chromatography was performed using a silica gel (Kieselgel 60, 70–230, and 230–400 mesh, Merck, Darmstadt, Germany), YMC C-18 resins, and thin layer chromatography (TLC) was performed using pre-coated silica-gel 60 F₂₅₄ and RP-18 F_254S plates (both 0.25 mm, Merck, Darmstadt, Germany). The spots were detected under UV light and using 10% H₂SO₄. The adjacent torsion angles were measured by Chemdraw 3D (version 17.1).