title: Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (alpha-hydroxyphosphonates).
abstract: The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.
authors.affiliation: Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan. hanaya@cc.okayama-u.ac.jp
authors.forename: Tadashi
authors.initials: T
authors.lastname: Hanaya
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Sugiyama
authors.forename: Heizan
authors.initials: H
authors.lastname: Kawamoto
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008968:Molecular Conformation; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005643:Fucose; D005947:Glucose; D008358:Mannose; D010100:Oxygen