Synthese von Cyclopropanphosphonatpyranosiden / Synthesis of Cyclopropylphosphonate Pyranosides

Ayjaz Fatima, Fakhar Zaman, Wolfgang Voelter
1991 Zeitschrift für Naturforschung. B, A journal of chemical sciences  
Reacting benzyl 2,3-anhydro-4-O-trifluoromethylsulfonyl-α-D-ribopyranoside (1) and benzyl 2,3-anhydro-4-O-trifluoromethylsulfonyl-β-L-ribopyranoside (2) with diethyl cyanomethylphosphonate the 3,4-cyclopropanated monosaccharide derivatives benzyl 3,4-(diethyl cyanomethylenephosphonate)-3,4-dideoxy-β-L-arabinopyranoside (5) and benzyl 3,4-(diethyl cyanomethylenephosphonate)-3,4-dideoxy-β-L-arabinopyranoside (6) are obtained. The 1H, 13C NMR and FD-MS data fully confirm the suggested structures.
more » ... he cyclopropanated sugar derivatives are of interest because of their structural relation to the antibiotic phosphonomycin.
doi:10.1515/znb-1991-0916 fatcat:p5hpzyh3cfdrzbbr7q4ugyop2y