Sepa 300 digital polarimeter

The following instruments were used to obtain spectroscopic data: specific rotations, Horiba SEPA-300 digital polarimeter (l = 5 cm); UV spectra, Shimadzu UV-1600 spectrometer; IR spectra, Shimadzu FTIR-8100 spectrometer; FAB-MS and high-resolution MS, JEOL JMS-SX 102A mass spectrometer; ESIMS and HRESIMS, Exactive Plus mass spectrometer (Thermo Fisher Scientific Inc., MA, USA); ¹H-NMR spectra, JEOL JNM-ECA600 (600 MHz) and JNM-ESC400 (400 MHz) spectrometers; ¹³C-NMR spectra, JEOL JNM-ECA600 (150 MHz) and JNM-ESC400 (100 MHz) spectrometers, with tetramethylsilane as an internal standard; HPLC detector, Shimadzu SPD-10Avp UV-VIS detectors; and HPLC column, Cosmosil 5C₁₈-MS-II (Nacalai Tesque Inc.). The following experimental conditions were used for column chromatography (CC): ordinary-phase silica gel CC, silica gel 60N (Kanto Chemical Co., Tokyo, Japan; 63–210 mesh, spherical, neutral), normal-phase thin-layer chromatography (TLC), pre-coated TLC plates with silica gel 60F₂₅₄ (Merck, Darmstadt, Germany; 0.25 mm), with detection achieved by spraying with 1% Ce(SO₄)₂–10% aqueous H₂SO₄, and followed by heating.

Specific rotation was measured with a Horiba SEPA-300 digital polarimeter (Kyoto, Japan, l = 5 cm) and IR spectra were collected on a Shimadzu FTIR-8100 spectrometer (Kyoto, Japan). For X-ray, a Bruker SMART-APEX II ULTRA (Billerica, MA, USA) was used. ESI-MS and HR-ESI-MS were carried out using a Thermo Fisher Scientific LTQ Orbitrap XL mass spectrometer (Waltham, MA, USA), and ¹H (600 MHz) and ¹³C (150 MHz) NMR spectra were recorded on a JEOL JNM-ECA 600 spectrometer (Tokyo, Japan) with tetramethylsilane as an internal standard. Purification was run on a Shimadzu HPLC system equipped with a RID-10A refractive index detector and compound separation was performed on YMC-Pack ODS-A (Tokyo, Japan, 250 × 4.6 mm i.d.) and (250 × 20 mm i.d.) columns for analytical and preparative separation, respectively. Chromatography separation included normal-phase silica BW-200 (Fuji Silysia Chemical, Ltd., Kasugai, Japan, 150–350 mesh) and ODS reverse phase Chromatorex DM1020T (Fuji Silysia Chemical, Ltd., 100–200 mesh) columns as well as silica gel 60_F254 (Merck, Darmstadt, Germany, 0.25 mm) and RP-18 WF_254S (Merck, 0.25 mm) TLC plates with spots developed with heating of H₂SO₄-MeOH (1:9) sprayed plates.