Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

Tadashi Hanaya, Ken Ichi Sugiyama, Heizan Kawamoto, Hiroshi Yamamoto

Research output: Contribution to journal › Article

17 Citations (Scopus)

Abstract

The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.

Original languageEnglish
Pages (from-to)1641-1650
Number of pages10
JournalCarbohydrate Research
Volume338
Issue number16
DOIs
Publication statusPublished - Jul 29 2003

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Stereoselectivity
Esterification
Chlorides
dimethyl hydrogen phosphite

Keywords

  • α-Hydroxyphosphonate
  • Deoxygenation
  • Phospho sugar

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates). / Hanaya, Tadashi; Sugiyama, Ken Ichi; Kawamoto, Heizan; Yamamoto, Hiroshi.

In: Carbohydrate Research, Vol. 338, No. 16, 29.07.2003, p. 1641-1650.

Research output: Contribution to journal › Article

Hanaya, T, Sugiyama, KI, Kawamoto, H & Yamamoto, H 2003, 'Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)', Carbohydrate Research, vol. 338, no. 16, pp. 1641-1650. https://doi.org/10.1016/S0008-6215(03)00235-0
Hanaya T, Sugiyama KI, Kawamoto H, Yamamoto H. Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates). Carbohydrate Research. 2003 Jul 29;338(16):1641-1650. https://doi.org/10.1016/S0008-6215(03)00235-0
Hanaya, Tadashi ; Sugiyama, Ken Ichi ; Kawamoto, Heizan ; Yamamoto, Hiroshi. / Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates). In: Carbohydrate Research. 2003 ; Vol. 338, No. 16. pp. 1641-1650.
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