Rxi 5ms column

All reactions were performed under an argon atmosphere unless otherwise stated. Commercially available starting materials were generously provided by Apollo Scientific and used without further purification. Tetrahydrofuran (THF) was freshly distilled from Na/benzophenone. Toluene for the Suzuki–Miyaura cross-coupling reactions was redistilled prior to use. Some of the compounds described in this article are known and have been previously reported; for compounds 1a, 2a, 11a, 12a, 1b, 2b, see reference [7 (link)], for compound 6a—[25 (link)], 8a—[9 (link)] and 9a—[17 (link)].
NMR spectra were recorded on a Bruker Avance III spectrometer (400 MHz for ¹H NMR and 100 MHz for ¹³C NMR). Chemical shifts δ are reported with respect to the residual solvent peak and are given in ppm. GC-MS analyses were performed on a Shimadzu GCMS-QP2010 ultra plus system using a Restek Rxi-5 ms column (30 m, 0.25 mmID). Reactions were monitored by TLC using Merk TLC silica gel 60 F₂₅₄ plates and visualized using UV light (254 nm) or KMnO₄ stain. Column chromatography was performed on ZEOprep 60 silica gel (35–70 µm, Apollo Scientific). Melting points were measured in open capillaries using a Mettler Toledo FP90 central processor equipped with Mettler Toledo FP81HT MBC cell.

Extraction of lipids for FA analysis was performed with chloroform/methanol (2:1 v/v), and FA methyl esters (ME) were prepared as described by Pérez-Palacios et al. [43 (link)]. The FA composition of pork meat was determined using gas chromatograph GC-2010 Plus (Shimadzu Corp., Kyoto, Japan) equipped with a mass spectrometer GCMS-QP2010 (Shimadzu Corp.). Separation was carried out on an Rxi-5 ms column (30 m length, 0.25 mm ID and 0.25 μm df (Restek, Bellefonte, PA, USA). The mass spectrometer was operated at full scan mode, and the analyte was injected in split mode at a 1:60 split ratio. The carrier gas was helium at a flow rate of 0.91 mL/min. The FAME concentration was determined using a calibration curve, and results were expressed as percentages of the total FAME concentration in the sample. The calibration curve was prepared using the standard Supelco 37 Component FAME Mix (Merck & Co., Inc., Kenilworth, NJ, USA).

¹H and ¹³C NMR experiments were performed in D₂O or CDCl₃ at 600 MHz for ¹H and 151 MHz for ¹³C nuclei on a Bruker Avance III Ultrashield 600. 2D NOE experiments were performed on a Bruker Avance-III-800 console equipped with a Bruker 18.8 T/54 mm Ascend Magnet at 25 °C. Preparative HPLC was conducted using an Agilent 1260 Infinity II LC equipped with an Agilent Eclipse XDB-C18 column (250 mm × 21.2 mm, 7 μm). Analytical HPLC was performed on an Agilent 1260 Infinity II system equipped with an Agilent 5 HC-C18(2) column (150 × 4.6 mm, 5 μm). GC-MS experiments were run on a ThermoScientific Trace GC Ultra spectrometer equipped with an Rxi-5MS column (Restek Corp., 30 m × 0.25 mm i.d., 0.25 μm df). The injection temperature was 250 °C, electron ionization was performed with 70 eV, ion source temperature was 250 °C, transfer line temperature was 280 °C, and mass scan range was from m/z 30–500 at 1500 μ s⁻¹. The program held at 50 °C for 3 min, increased the temperature at a rate of 20 °C min⁻¹ up to 300 °C, and then was maintained at 300 °C for 3 min. Optical rotations were measured on a JASCO P-1010 polarimeter.