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

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

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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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Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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