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
Publication statusPublished - Jul 1 2001

Fingerprint

Hydrochloric Acid
Galactose
Sugars
Hydroxyl Radical
Hydrogen Peroxide
Magnetic Resonance Spectroscopy
Sodium
Derivatives
Addition reactions
Nuclear magnetic resonance spectroscopy
Conformations
propylene
dihydrobis(2-methoxyethoxy)aluminate
Proton Magnetic Resonance Spectroscopy
dimethyl hydrogen phosphite

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hanaya, T., Sugiyama, K. I., Fujii, Y., Akamatsu, A., & Yamamoto, H. (2001). Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose. Heterocycles, 55(7), 1301-1309.

Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives : New phospha-sugar analogs of D-galactose. / Hanaya, Tadashi; Sugiyama, Ken Ichi; Fujii, Yasushi; Akamatsu, Akihito; Yamamoto, Hiroshi.

In: Heterocycles, Vol. 55, No. 7, 01.07.2001, p. 1301-1309.

Research output: Contribution to journalArticle

Hanaya, T, Sugiyama, KI, Fujii, Y, Akamatsu, A & Yamamoto, H 2001, 'Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose', Heterocycles, vol. 55, no. 7, pp. 1301-1309.
Hanaya, Tadashi ; Sugiyama, Ken Ichi ; Fujii, Yasushi ; Akamatsu, Akihito ; Yamamoto, Hiroshi. / Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives : New phospha-sugar analogs of D-galactose. In: Heterocycles. 2001 ; Vol. 55, No. 7. pp. 1301-1309.
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AU - Yamamoto, Hiroshi

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