Synthesis and reactions of 2',3'-anhydro-1-β-d-ribofuranosyl-uracil derivatives

molecular structures of 3-methyl-2',3'-anhydrouridine and 3,5-dimethyl-2',3':O6,5'-dianhydrouridine

M. Màrton-Merész, J. Kuszmann, I. Pelczer, L. Párkányí, T. Koritsànszky, A. Kálmán

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

2',3'-anhydro-1-β-D-ribofuranosyl-uracil derivatives, which are formed under basic conditions in an equilibrium from the corresponding 2,2'-anhydro isomers could be trapped by 3-N-methylation (3,8). The 3-methyl-5-bromo-2', 3'-epoxide 8 gave on further methylation the 5-methyl-2',3':O6,5'-dianhydro derivative 16, representing a method for converting uracil derivatives into thymidine nucleosides. The 2',3'-epoxides could be hydrolyzed to the corresponding arabinosyl derivatives, whereas 2'-bromo-2'-deoxy nucleosides with "ribo" configuration were obtained on treatment with HBr. All structures were proved by 1H NMR. The molecular structures of 3 and 16 were also substantiated by X-ray analysis. The impact of the oxirane rings and the additional O6-5'-ring closure on the puckering of the ribofuranose moiety is discussed.

Original languageEnglish
Pages (from-to)275-284
Number of pages10
JournalTetrahedron
Volume39
Issue number2
DOIs
Publication statusPublished - 1983

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Uracil
Molecular Structure
Nucleosides
Methylation
Molecular structure
Derivatives
Ethylene Oxide
Epoxy Compounds
Thymidine
X-Rays
X ray analysis
Isomers
Nuclear magnetic resonance
Proton Magnetic Resonance Spectroscopy
Epoxide 8

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and reactions of 2',3'-anhydro-1-β-d-ribofuranosyl-uracil derivatives : molecular structures of 3-methyl-2',3'-anhydrouridine and 3,5-dimethyl-2',3':O6,5'-dianhydrouridine. / Màrton-Merész, M.; Kuszmann, J.; Pelczer, I.; Párkányí, L.; Koritsànszky, T.; Kálmán, A.

In: Tetrahedron, Vol. 39, No. 2, 1983, p. 275-284.

Research output: Contribution to journalArticle

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AB - 2',3'-anhydro-1-β-D-ribofuranosyl-uracil derivatives, which are formed under basic conditions in an equilibrium from the corresponding 2,2'-anhydro isomers could be trapped by 3-N-methylation (3,8). The 3-methyl-5-bromo-2', 3'-epoxide 8 gave on further methylation the 5-methyl-2',3':O6,5'-dianhydro derivative 16, representing a method for converting uracil derivatives into thymidine nucleosides. The 2',3'-epoxides could be hydrolyzed to the corresponding arabinosyl derivatives, whereas 2'-bromo-2'-deoxy nucleosides with "ribo" configuration were obtained on treatment with HBr. All structures were proved by 1H NMR. The molecular structures of 3 and 16 were also substantiated by X-ray analysis. The impact of the oxirane rings and the additional O6-5'-ring closure on the puckering of the ribofuranose moiety is discussed.

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