IR analyses were performed at CUTAM, Sivas Cumhuriyet University, Turkey, and at Research Laboratory Centre, Erciyes University, Kayseri, Turkey. High-Performance Liquid Chromatography, and arbon and proton NMRs were performed at Research Laboratory Centre, Erciyes University, Kayseri, Turkey. Mass Spectrometry analyses were performed at Research Laboratory Centre, Istanbul University, Istanbul, Turkey. HPLC (Agilent 1260) was used for assessing the conversion percentage of sugar monomers into sugar-fatty acid ester using an Agilent ZORBAX Carbohydrate Analysis Column. IR (Perkin Elmer 400) , Nuclear Magnetic Resonance ( 1 H-NMR, Varian UNITY INOVA 500 MHz; 13 C-NMR Bruker spectrometer, 125 MHz) , and Mass Spectrometry (Thermo Finnigan LCQ LC-MS/MS Spectrometer) were used for the structural analysis of the ester products.
Unity inova 500 mhz
Manufactured by Bruker
The UNITY INOVA 500 MHz is a high-performance nuclear magnetic resonance (NMR) spectrometer designed for analytical and research applications. It operates at a frequency of 500 MHz and is capable of providing detailed structural information about molecules and materials. The core function of this equipment is to analyze and characterize the chemical composition and structure of various samples through the use of NMR spectroscopy.
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Lab products found in correlation
Zorbax carbohydrate analysis column, by Agilent Technologies (1 mentions)
Autopal 4 automatic polarimeter, by Rudolph Research Analytical (1 mentions)
Uv 1800 spectrophotometer, by Thermo Fisher Scientific (1 mentions)
Q tof ultima esi tof mass spectrometer, by Agilent Technologies (1 mentions)
Nicolet is50 ftir spectrometer, by Thermo Fisher Scientific (1 mentions)
Ir 470 spectrometer, by Shimadzu (1 mentions)
Avance drx 400 nmr spectrometer, by Bruker (1 mentions)
3 protocols using unity inova 500 mhz
1
Analytical Characterization of Sugar-Fatty Acid Esters
2
Characterization of Novel Compound
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Optical rotations were measured with a Rudolph Research Analytical Autopal IV Automatic polarimeter. Ultraviolet and infrared spectra were obtained with Shimadzu UV-1800 spectrophotometer and ThermoScientific Nicolet iS50FT-IR spectrometer, respectively. NMR spectra were recorded in Acetone-d6 with 2 drops of DMSO-d6 on Varian Unity Inova 500 MHz and Bruker 400 MHz; high resolution mass spectra were obtained an Agilent Q-TOF Ultima ESI-TOF mass spectrometer. Preparative HPLC was carried out on a ThermoScientific U3000 LC system. Extensive multidimensional NMR supporting data are found in the SI Appendix .
3
Synthesis of Phosphonated Cyclopentenone Derivatives
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All solvents and chemicals were purchased from commercial sources and used without further purification. The utilized ethyl arylmethylidincyanoacetates were prepared by the Knovenagel condensation of aldehydes with ethyl cyanoacetate on the basis of the reported procedure [19] (link). Melting points were determined on a Melt-Tem II melting point apparatus and are uncorrected. IR spectra were recorded on a Shimadzu IR-470 spectrometer. All the NMR spectra were recorded on a Varian model UNITY Inova 500 MHz or Bruker DRX-400 Avance NMR spectrometer. Chemical shifts of 1 H, 13 C and 31 P NMR are reported in parts per million (ppm) from tetramethylsilane (TMS) as an internal standard or 85% H 3 PO 4 as external standard in DMSO-d 6 as solvent.
General procedure for synthesis of phosphonated cyclopentenone derivatives 4a-o.
DAAD (1.0 mmol) was added dropwise to the mixture of trialkyl phosphite (1.0 mmol), ethyl arylmethylidincyanoacetate (1.0 mmol) and NaN 3 (0.1 mmol) in acetone at room temperature. The reaction mixture was then stirred at room temperature for 12 hours. The solvent was removed under reduced pressure, and the solid residue was washed with water (15 mL) and diethyl ether (15 mL) to afford the pure phosphonated cyclopentenone derivative.
General procedure for synthesis of phosphonated cyclopentenone derivatives 4a-o.
DAAD (1.0 mmol) was added dropwise to the mixture of trialkyl phosphite (1.0 mmol), ethyl arylmethylidincyanoacetate (1.0 mmol) and NaN 3 (0.1 mmol) in acetone at room temperature. The reaction mixture was then stirred at room temperature for 12 hours. The solvent was removed under reduced pressure, and the solid residue was washed with water (15 mL) and diethyl ether (15 mL) to afford the pure phosphonated cyclopentenone derivative.
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