Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (alpha-hydroxyphosphonates).
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.
Hanaya
Tadashi
T
Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan. hanaya@cc.okayama-u.ac.jp
Sugiyama
Ken-ichi
K
Kawamoto
Heizan
H
Yamamoto
Hiroshi
H
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
D005643:Fucose; D005947:Glucose; D008358:Mannose; D010100:Oxygen