Synthesis of Sugar Analogs Having a Phosphorus Atom in the Hemiacetal Ring (Phosphoro Sugar)

Tadashi Hanaya, Hiroshi Yamamoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Synthetic studies are reviewed on sugar analogs containing a phosphorus atom in the hemiacetal ring, e.g., analogs of d-xylo, d-gluco, 6-deoxy-l-galacto. d-mannopyranoses, as well as d-ribo and 2-deoxy-d-ribofuranoses. These compounds were converted into the corresponding per-O-acetyl derivatives, whose structures and conformations were established by 1H-NMR spectral analyses and partly by X-ray crystallographic analyses. Stereoselectivity of the introduction of a phosphinyl group to various types of 6-O-tosyl-hex-5-uloses and 6-nitro-hex-5-enoses are also described.

Original languageEnglish
Pages (from-to)377-387
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume51
Issue number5
DOIs
Publication statusPublished - 1993

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Stereoselectivity
Sugars
Phosphorus
Conformations
Nuclear magnetic resonance
Derivatives
X rays
Atoms

Keywords

  • Addition of phosphonate
  • C-P bond
  • Chemical modification of carbohydrate
  • Cyclic phosphorus compound
  • Phosphoro sugar

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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AU - Hanaya, Tadashi

AU - Yamamoto, Hiroshi

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AB - Synthetic studies are reviewed on sugar analogs containing a phosphorus atom in the hemiacetal ring, e.g., analogs of d-xylo, d-gluco, 6-deoxy-l-galacto. d-mannopyranoses, as well as d-ribo and 2-deoxy-d-ribofuranoses. These compounds were converted into the corresponding per-O-acetyl derivatives, whose structures and conformations were established by 1H-NMR spectral analyses and partly by X-ray crystallographic analyses. Stereoselectivity of the introduction of a phosphinyl group to various types of 6-O-tosyl-hex-5-uloses and 6-nitro-hex-5-enoses are also described.

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