An efficient synthesis of certain 5-substituted-2'-deoxyuridine 3',5'-cyclic monophosphate p-o-alkyl(aralkyl) esters. The crystal and molecular structure of 5-IODO-2'-deoxyuridine 3',5'-cyclic monophosphate p-o-methyl ester with axial methoxy group

J. Béres, P. Sándor, A. Kálmán, T. Koritsánszky, L. ötvös

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Some 5-alkyl- and 5-halogeno-2'-deoxyuridine 3',5'-cyclic mono- phosphate P-O-alkyl(aralkyl) esters have been prepared from the silver salts of the parent cyclic monophosphates and alkyl(aralkyl) iodides. The diastereomeric phosphotriesters have been characterized by spectroscopic methods. The crystal and molecular structure of 5-iodo-2'-deoxyuridine 3',5'-cyclic monophosphate P-O-methyl ester with axial methoxy group has been determined. We failed to obtain the desired triesters from the reactions of the cAMP silver salt with alkyl iodides, contrary to previous claims in the literature.

Original languageEnglish
Pages (from-to)2405-2414
Number of pages10
JournalTetrahedron
Volume40
Issue number12
DOIs
Publication statusPublished - 1984

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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