Avance 3 700 ft nmr

Specific rotation, PerkinElmer 343 Polarimeter (PerkinElmer, Waltham, MA, USA); NMR, Bruker Avance III 700 Bruker FT-NMR (Bruker BioSpin GmbH, Rheinstetten, Germany) (700.00/176.03 MHz) (¹H/¹³C) spectrometer; ESI MS (positive and negative ion modes), Agilent 6510 Q-TOF apparatus (Agilent Technology, Santa Clara, CA, USA), sample concentration 0.01 mg/mL; HPLC, Agilent 1260 Infinity II with a differential refractometer (Agilent Technology, Santa Clara, CA, USA); columns Supelcosil LC-Si (4.6 × 150 mm, 5 μm) and Ascentis RP-Amide (10 × 250 mm, 5 μm) (Supelco, Bellefonte, PA, USA), Phenomenex Synergi Fusion RP (10 × 250 mm, 5 μm) (Phenomenex, Torrance, CA, USA).

Optical rotations were measured on a Perkin-Elmer 343 digital polarimeter (Perkin Elmer, Waltham, MA, USA). The ¹H and ¹³C NMR spectra were recorded in CDCl₃ using Bruker Avance III 500 (Bruker BioSpin GmbH, Rheinstetten, Germany) (500.13/125.77 MHz) or Avance III 700 Bruker FT-NMR (Bruker BioSpin GmbH, Rheinstetten, Germany) (700.13/176.04 MHz) spectrometers. HRESI and ESI mass spectra were recorded on an Agilent 6510 Q-TOF LC/MS mass spectrometer (Agilent Technologies, Santa Clara, CA, USA), and samples were dissolved in methanol (c 0.01 mg/mL). TLC was carried out on silica gel plates (CTX-1A, 5-17 µm, Sorbfil, Russia) and spots were visualized by spraying with aqueous 10% H₂SO₄ followed by heating. Column chromatography (CC) was performed on silica gel (KSK, 50−160 mesh, Sorbfil, Russia) and YMC ODS-A (12 nm, S-75 um, YMC Co., Ishikawa, Japan). HPLC was performed using an Agilent 1100 Series chromatograph with a differential refractometer (Agilent Technologies, Santa Clara, CA, USA). The reversed-phase columns (YMC-Pack ODS-A, YMC Co., Ishikawa, Japan, 10 mm × 250 mm, 5 µm and 4.6 mm × 250 mm, 5 µm) and normal-phase column (Ultrashere-Si, Beckman Instruments, Inc., Berkeley, CA, USA, 10 mm × 250 mm, 5 µm) were used for HPLC. Yields are based on dry weight of the sponge.

We used for specific rotation a Perkin-Elmer 343 Polarimeter (Perkin-Elmer, Waltham, MA, USA); for NMR, a Bruker Avance III 700 Bruker FT-NMR (Bruker BioSpin GmbH, Rheinstetten, Germany) (700.00/176.03 MHz) (¹H/¹³C) spectrometer; for ESI MS (positive and negative ion modes), an Agilent 6510 Q-TOF apparatus (Agilent Technology, Santa Clara, CA, USA), sample concentration of 0.01 mg/mL; and for HPLC, an Agilent 1100 apparatus with a differential refractometer (Agilent Technology, Santa Clara, CA, USA). The column was a Supelco Discovery HS F5-5 (10 × 250 mm, 5 μm) (Supelco, inc., Bellefonte, PA, USA).