Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases

Akira Sakakura, Mikimoto Katsukawa, Kazuaki Ishihara

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

(Chemical Equation Presented) Phosphate monoesters are synthesized from a mixture of phosphoric acid (1 or 2 equiv) and alcohols (1 equiv) in the presence of tributylamine. The reaction is promoted by nucleophilic bases such as N-alkylimidazole and 4-(N,N-dialkylamino)pyridine. 2′,3′-I- Isopropylidene ribonucleosides are selectively converted to their 5′-monophosphates without the protection of amino groups in nucleobases.

Original languageEnglish
Pages (from-to)1999-2002
Number of pages4
JournalOrganic Letters
Volume7
Issue number10
DOIs
Publication statusPublished - May 12 2005
Externally publishedYes

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Ribonucleosides
phosphoric acid
Condensation
pyridines
phosphates
alcohols
condensation
Phosphates
Alcohols
synthesis
pyridine
propylene
tributylamine

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases. / Sakakura, Akira; Katsukawa, Mikimoto; Ishihara, Kazuaki.

In: Organic Letters, Vol. 7, No. 10, 12.05.2005, p. 1999-2002.

Research output: Contribution to journalArticle

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