Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides

Paolo Ronchi, Stefano Vignando, Sara Guglieri, Laura Polito, Luigi Lay
2009 Organic and biomolecular chemistry  
Electronic Supporting Information Additional experimental procedures, analytical data and copies of NMR spectra. General Procedures. NMR spectra were recorded on Bruker AC 300, Bruker Avance 400 and Bruker Avance 500 spectrometers at 298 K, if not differently reported. In 13 C NMR spectra, signals corresponding to aromatic carbons are omitted. Chemical shifts are reported on the δ (ppm) scale and the coupling costants are given in Hz. When possible, peaks assignments were based on the analysis
more » ... f 2D spectra (H,H-COSY and HSQC or HMQC spectra). In particular, due to the scarce amount of available sample, 13 C assignment of compounds 36/37 has been based exclusively on HSQC spectrum. HRMS spectra were recorded in positive mode on Bruker Daltonics APEX TM II (FT-ICR). Optical rotations were measured at room temperature with a Perkin-Elmer 241 polarimeter. HPLC analyses were performed with Varian 9050. Column Lichrocart 125-4 RP-18 5μm, flow rate 1 mL min -1 , UV monitor λ=210 nm. In all HPLC analyses, acetonitrile-water mixtures were used as eluent. TLC and HPTLC were carried out on Merck Silica-gel 60 F-254 plates (0.25 mm and 0.2 mm thickness respectively), and spots were visualized by spraying with a solution containing H 2 SO 4 (31 mL), ammonium molybdate (21 g) and Ce(SO 4 ) 2 (1 g) in 500 mL water, followed by heating at 110 °C for 5 min. Column chromatography was performed by the flash procedure using Merck Silicagel 60 (230-400 mesh). Solvents were dried by standard procedures. Supplementary Material (ESI)
doi:10.1039/b822989a pmid:19503940 fatcat:ker4fg7k4rhhddnq2ugal4tz6y