Notizen: Synthese und NMR-spektroskopische Eigenschaften von Benzyl-2,3-anhydro-4-desoxy-4-[N]-pyridinium-pyranosiden/Synthesis and NMR Spectroscopic Properties of Several Benzyl 2,3-Anhydro-4-deoxy-4-[N]-pyridinium Pyranosides

Wolfgang Kowollik, Wolfgang Voelter
1992 Zeitschrift für Naturforschung. B, A journal of chemical sciences  
Benzyl 2,3-anhydro-4-0-triflyl-β-L-ribopyranoside (1) and benzyl 2,3-anhydro-4-O-triflyl-α-D-lyxopyranoside (3) react with pyridine to give benzyl 2,3-anhydro-4-deoxy-4-[N]-pyridinium - α-D-lyxopyranoside triflate (2) and benzyl 2,3-anhydro-4-deoxy-4-[N]-pyridinium -β-L-ribopyranoside triflate (4). Similar reactions with thiourea and dimethylsulfoxide are mentioned. Compound 2 is stable at room temperature, whereas compound 4 decomposes in a few hours (neighbouring group effect). The 13C NMR
more » ... ignments of 2 are proved by 13C {1H} single frequency decoupling experiments.
doi:10.1515/znb-1992-0421 fatcat:taesmktkcbfabjtobtom66z4aq