Boronic acid mono- and diesters of the aldopentoses.
The four aldopentoses ribose, arabinose, xylose, and lyxose were evaluated to test their suitability as linear linkers for the formation of intrinsically chiral covalent organic boronic ester networks. Based on X-ray crystal structures of the reaction products with phenylboronic acid, arabinose and xylose formed boronic acid diesters. Lyxose and ribose formed monoesters under the conditions employed. NMR shielding constants were calculated by DFT methods. The results are highly correlated with the experimentally observed NMR shift values.
Reichvilser
Moritz M
MM
Ludwig-Maximilians-Universität, Department Chemie und Biochemie, München, Germany.
Heinzl
Christoph
C
Klüfers
Peter
P
D000465:Algorithms; D001089:Arabinose / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010429:Pentoses / Q000737:chemistry*; D014961:X-Ray Diffraction; D014994:Xylose / Q000737:chemistry
D001897:Boronic Acids; D004952:Esters; D010429:Pentoses; D014994:Xylose; D001089:Arabinose; C010686:benzeneboronic acid