Adenosine cyclic 3′,5′-(RP)- and (SP)-phosphoramidates, the first representatives of nucleoside cyclic 3′,5′-phosphoramidates derived from ammonia

S. Bottka, J. Tomasz

Research output: Article

8 Citations (Scopus)

Abstract

Adenosine cyclic 3′,5′-phosphoramidate 2 was synthesized by reacting adenosine cyclic 3′,5′-phosphate 1 with POCl3, in trimethyl phosphate for 1 h at O°C, followed by in situ treatment of the reaction mixture with a suspension of (NH4)2CO3 in anhydrous DMF or pyridine or DMF/pyridine mixture for 30 min at 25° C. Diastereoisomers (RP)-2 and (SP)-2 the relative quantities of which depended on the solvent of (NH4)2CO3 treatment, were separated by reversed phase partition chromatography. Hydrolysis of (RP)-2 and (SP)-2 proceeded with predominant (90% in 0.1 N HCl, 100% in 0.1 N NaOH) -P-O-C bond breaking.

Original languageEnglish
Pages (from-to)2909-2912
Number of pages4
JournalTetrahedron Letters
Volume26
Issue number24
DOIs
Publication statusPublished - 1985

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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