137157-11-0Relevant academic research and scientific papers
SPIN LABELLED C-GLYCOSIDE ANALOGS: DERIVATIVES OF 1,4-ANHYDRO-4-DEOXY-2,3-O-CYCLOPENTYLIDENE-1,4-N-HYDROXYIMINO-DL-ERYTHROFURANOSE
Tronchet, Jean M. J.,Balkadjian, Mirna,Zosimo-Landolfo, Guido,Barbalat-Rey, Francoise,Lichtle, Patrick,et al.
, p. 17 - 34 (2007/10/02)
A series of 2,3-O-cyclopentylidene C-glycoside analogs in which the furanose ring has been replaced with a N-hydroxypyrrolidine have been prepared.A structural study of these tricyclic compounds and the aminoxyl radicals thereof has been carried out using variable temperature 1H NMR, X-ray diffraction, molecular dynamics and EPR spectroscopy.Both types of compounds, N-hydroxypyrrolidines and pyrrolidine N-oxyls, fundamentally prefer - in solutions - N-endo conformations over the alternate, N-exo forms found by X-ray diffraction studies and computed to be more stable by molecular dynamics.
New Types of Spin-labelled Sugar and Nucleoside Analogs: Pyrrolidine, Morpholine and Piperidine N-Oxyls
Tronchet, Jean M. J.,Zosimo-Landolfo, Guido,Balkadjian, Mirna,Ricca, Alessandra,Zsely, Martina,et al.
, p. 4129 - 4132 (2007/10/02)
Analogs of blocked furanose (20) or pyranose sugars (i.e. 15) and of nucleosides (i.e. 23) in which the ring oxygen has been replaced with a -N(OH)- bridge have been prepared in generally good yields by a general reductive cyclization procedure preserving the configuration of the preexistant asymetric centers and proceeding stereoselectively (in more favorable cases stereospecifically) when creating a new asymetric center.The title compounds oxidised to nitroxide free radicals affording usable ESR spectra.Keywords: ESR; Nitroxides; Hydroxylamines; Reductive Cyclization; Nitrones
