Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose

Tadashi Hanaya, Ken Ichi Sugiyama, Yasushi Fujii, Akihito Akamatsu, Hiroshi Yamamoto

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-α-L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by 1H-NMR spectroscopy.

Original languageEnglish
Pages (from-to)1301-1309
Number of pages9
JournalHeterocycles
Volume55
Issue number7
DOIs
Publication statusPublished - Jul 1 2001

Keywords

  • C-P bond
  • Deoxygenation
  • Heterosugar
  • Hexofuranos-5-ulose
  • Phosphorinane

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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