Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-D-fructopyranose derivatives.
3,4-Di-O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-beta-D-fructofuranose (13) was prepared from the known 1,2-O-isopropylidene-6-O-tosyl-beta-D-fructofuranose in five steps. Reduction of 13 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the 6-deoxy-6-hydroxyphosphinyl-D-fructopyranose derivative. This was converted into the 1,2,3,4,5-penta-O-acetyl-6-deoxy-6-methoxyphosphinyl-D-fructopyranoses, whose structure and conformation were established by 1H NMR spectroscopy.
Hanaya
Tadashi
T
Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan. hanaya@cc.okayama-u.ac.jp
Imai
Kumiko
K
Prikhod'ko
Yurij V
YV
Yamamoto
Hiroshi
H
D005632:Fructose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010759:Phosphorus Isotopes
D009943:Organophosphorus Compounds; D010759:Phosphorus Isotopes; D005632:Fructose