title: Phenylboronic acid esters of the common 2-deoxy-aldoses.
abstract: Phenylboronic acid esters are formed by the three common 2-deoxy aldoses: 2-deoxy-d-erythro-pentose ('2-deoxy-d-ribose'), 2-deoxy-d-lyxo-hexose ('2-deoxy-d-galactose'), and 2-deoxy-d-arabino-hexose ('2-deoxy-d-glucose'). The major species that was formed from equimolar quantities of boronic acid and the aldose, was the 3,4-monoester of the pentopyranose in a skew-boat conformation, and the 4,6-monoester in the case of the two hexopyranoses. A double molar quantity of boronic acid led, for both 2-deoxy-hexoses, to the diester of the open-chain aldehydo isomer as the major product: the 3,5:4,6-diester for the lyxo-configured deoxy-hexose, and the 3,4:5,6-diester of the arabino-configured isomer. Minor products of all reactions were identified by a combined NMR/DFT methodology.
authors.affiliation: Ludwig-Maximilians-Universität, Department Chemie, Butenandtstraße 5-13, München, Germany.
authors.forename: David
authors.initials: D
authors.lastname: Hess
authors.forename: Peter
authors.initials: P
authors.lastname: Klüfers
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010429:Pentoses / Q000737:chemistry
chemical_list: D001897:Boronic Acids; D004952:Esters; D010429:Pentoses; C019327:2-deoxy-lyxo-hexose; C010686:benzeneboronic acid; D005690:Galactose