Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives

Tadashi Hanaya, Kumiko Imai, Yurij V. Prikhod'Ko, Hiroshi Yamamoto

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

3,4-Di-O-benzyl-6-deoxy-6-diethoxyphosphinyl-1,2-O-isopropylidene-β-d- fructofuranose (13) was prepared from the known 1,2-O-isopropylidene-6-O-tosyl- β-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.

Original languageEnglish
Pages (from-to)31-37
Number of pages7
JournalCarbohydrate Research
Volume340
Issue number1
DOIs
Publication statusPublished - Jan 17 2005

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Structural analysis
Derivatives
Rubiaceae
Hydrochloric Acid
Hydrogen Peroxide
Nuclear magnetic resonance spectroscopy
Conformations
Magnetic Resonance Spectroscopy
Sodium
propylene
dihydrobis(2-methoxyethoxy)aluminate
Proton Magnetic Resonance Spectroscopy

Keywords

  • 6-Deoxy-6-phosphinyl-d-fructopyranose
  • Acetyl migration
  • Conformational analysis
  • Hydroxyphosphinyl group
  • Phospho sugar

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives. / Hanaya, Tadashi; Imai, Kumiko; Prikhod'Ko, Yurij V.; Yamamoto, Hiroshi.

In: Carbohydrate Research, Vol. 340, No. 1, 17.01.2005, p. 31-37.

Research output: Contribution to journalArticle

Hanaya, Tadashi ; Imai, Kumiko ; Prikhod'Ko, Yurij V. ; Yamamoto, Hiroshi. / Synthesis and structural analysis of 6-deoxy-6-hydroxyphosphinyl-d- fructopyranose derivatives. In: Carbohydrate Research. 2005 ; Vol. 340, No. 1. pp. 31-37.
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