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1

Spectroscopic Analysis of Organic Compounds

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Optical rotations were measured on a JASCO DIP-1000 polarimeter, with a Na (589 nm) lamp and filter. IR spectra were measured on a FTIR Bruker Vector 22 spectrometer. 1H, 13C, and 2D NMR spectra were recorded on a Bruker Avance 500 spectrometer at 500 and 125 MHz, respectively, using CDCl3. Low resolution electrospray mass spectrometry (LRESIMS) and high resolution electrospray mass spectrometry (HRESIMS) experiments were performed on the Applied Biosystems QSTAR Elite system. LREIMS and HREIMS were performed on the Mass Spectrometer Thermo MAT95XP. HPLC separations were performed on the Agilent 1100 liquid chromatography system equipped with a solvent degasser, quaternary pump, and diode array detector (Agilent Technologies, Waldbronn, Germany) using a semipreparative reversed phase column Luna C18, 5 µ, 100 Å, 250 × 10 mm. Precoated silica gel plates (Merck, Kieselgel 60 F254, 0.25 mm) were used for TLC analysis, and the spots were visualized under a UV light (254 nm) or by heating the plate pretreated with H2SO4/H2O/AcOH (1:4:20).
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2

Spectroscopic Characterization of Organic Compounds

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Optical rotations were measured on a JASCO DIP-1000 polarimeter, with a Na (589 nm) lamp and filter. IR spectra were measured on a FTIR Bruker Vector 22 spectrometer. 1H, 13C, and 2D NMR spectra were recorded on a Bruker Avance 500 spectrometer at 500 and 125 MHz, respectively, using CDCl3. Low resolution electrospray mass spectrometry (LRESIMS) and high-resolution electrospray mass spectrometry (HRESIMS) experiments were performed on the Applied Biosystems QSTAR Elite system. The chemical shifts were given in δ (ppm) and coupling constants in Hz. HPLC separations were performed on the Agilent 1100 liquid chromatography system equipped with a solvent degasser, quaternary pump, and diode array detector (Agilent Technologies, Waldbronn, Germany) using a semipreparative normal phase column Nova-pak, silica 6 µm 60 Å, 300 × 7.8 mm (Waters). Precoated silica gel plates (Merck, Kieselgel 60 F254, 0.25 mm) were used for TLC analysis, and the spots were visualized under a UV light (254 nm) or by heating the plate pre-treated with H2SO4/H2O/AcOH (1:4:20)25 (link).
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3

Optical Rotations and NMR Spectroscopy Protocol

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Optical rotations were measured on a JASCO DIP-1000 polarimeter, with an Na (589 nm) lamp and filter. 1H, 13C, and 2D NMR spectra were recorded on a Bruker spectrometer of 950 MHz, equipped with a 5 mm Cryo Probe (NEO console); a Bruker spectrometer (800 MHz for 1H and 200 MHz for 13C) equipped with a 5 mm Cryo Probe and an NEO console; a Bruker (800 MHz for 1H and 200 MHz for 13C) spectrometer equipped with a 3 mm Cryo Probe and a NEO console; a Bruker spectrometer (700 MHz for 1H and 175 MHz for 13C) equipped with a 5 mm Cryo Probe and an Avance III console; and a Bruker Avance 500 spectrometer (500 MHz for 1H and 125 MHz for 13C) equipped with a 5 mm Cryo Probe, using DMSO-d6 and CDCl3 as solvents. Chemical shifts are reported in δ scale relative to DMSO-d6 (δ 2.50 ppm for 1H NMR, δ 39.51 ppm for 13C NMR) and CDCl3 (δ 7.26 ppm for 1H NMR, δ 77.0 ppm for 13C NMR).
HRESIMS experiments were performed on the Applied Biosystems QSTAR Elite system or a Thermo MAT95XP spectrometer. HPLC separations were performed on the Agilent 1100 liquid chromatography system equipped with a solvent degasser, quaternary pump, and diode array detector (Agilent Technologies, Waldbronn, Germany) using a semipreparative reversed phase column Luna C18 (5 μ, 100 Å, 250 × 10 mm).
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4

Characterization of Organic Compounds

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Optical rotations were measured in a JASCO DIP-1000 polarimeter (JASCO, Tokyo, Japan), with a Na (589 nm) lamp and filter. 1H, 13C and 2D NMR spectra were recorded in a Bruker Avance 500 spectrometer, at 500 and 125 MHz, respectively, with CD3OD and D2O as solvents. HRESIMS experiments were performed in an Applied Biosystems QSTAR Elite system or a Thermo MAT95XP spectrometer. HPLC separations were performed in the Agilent 1100 liquid chromatography system equipped with a solvent degasser, quaternary pump, and diode array detector (Agilent Technologies, Waldbronn, Germany) with a semipreparative reversed phase column (Luna C18: 5 μ, 100 Å, 250 × 10 mm, Phenomenex, Lane Cove, Australia). Precoated silica gel plates (Merck, Kieselgel 60 F254, 0.25 mm, Merck Millipore, Merck KGaA, Darmstadt, Germany) were used for TLC analysis and the spots were visualized under a UV light (254 nm) or by heating the plate pretreated with H2SO4/H2O/AcOH (1:4:20).
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