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

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

Research output: Contribution to journalArticle

20 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

Keywords

  • Deoxygenation
  • Phospho sugar
  • α-Hydroxyphosphonate

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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