Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters

Naoki Mitsuo, Yoshihiro Abe, Takeo Takizawa, Takehisa Kunieda

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

1-Alkenyl and phenyl phosphate esters undergo smooth cleavage of the phosphorus-oxygen linkage by fluoride-catalyzed alcoholysis to give aldehydes (ketones) and phenols, respectively. Application of this method provides a new route to 2-deoxyaldosugars from the enol-phosphates derived from vinylene carbonate telomers.

Original languageEnglish
Pages (from-to)1327-1330
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume28
Issue number4
DOIs
Publication statusPublished - 1980
Externally publishedYes

Fingerprint

Fluorides
Esters
Phosphates
Phenols
Ketones
Aldehydes
Phosphorus
Oxygen
vinylene carbonate

Keywords

  • 2-deoxyaldose
  • aryl phosphate
  • cesium fluoride
  • enol phosphate
  • vinylene carbonate telomer

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters. / Mitsuo, Naoki; Abe, Yoshihiro; Takizawa, Takeo; Kunieda, Takehisa.

In: Chemical and Pharmaceutical Bulletin, Vol. 28, No. 4, 1980, p. 1327-1330.

Research output: Contribution to journalArticle

Mitsuo, Naoki ; Abe, Yoshihiro ; Takizawa, Takeo ; Kunieda, Takehisa. / Synthetic Route to 2-Deoxyaldoses by Fluoride-Catalyzed Solvolysis of Enol-Phosphate Esters. In: Chemical and Pharmaceutical Bulletin. 1980 ; Vol. 28, No. 4. pp. 1327-1330.
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