5'-Substituted 2,2'-anhydrouridines

M. Merész, P. Sohár, J. Kuszmann

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

3',5'-Di-O-acetyl-2'-halogenouridines (1a, 1c and 1d) can be partially deacetylated at C-5' by transesterification with methanol-HCl, providing the 3'-O-acetyl derivatives 2a-2c. These can be converted into the 5'-O-mesyl derivatives 3a-3c, and latter into the 5'-chloro compounds 3d-3f. All 5'-substituted 2'-halogeno compounds give the corresponding 2,2'-anhydrouridine derivatives 4a-4c on treatment with NaOMe. Structures were proved by IR and 1H-NMR.

Original languageEnglish
Pages (from-to)2131-2133
Number of pages3
JournalTetrahedron
Volume33
Issue number16
DOIs
Publication statusPublished - 1977

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Methanol
Derivatives
Transesterification
Nuclear magnetic resonance
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

5'-Substituted 2,2'-anhydrouridines. / Merész, M.; Sohár, P.; Kuszmann, J.

In: Tetrahedron, Vol. 33, No. 16, 1977, p. 2131-2133.

Research output: Contribution to journalArticle

Merész, M, Sohár, P & Kuszmann, J 1977, '5'-Substituted 2,2'-anhydrouridines', Tetrahedron, vol. 33, no. 16, pp. 2131-2133. https://doi.org/10.1016/0040-4020(77)80327-X
Merész, M. ; Sohár, P. ; Kuszmann, J. / 5'-Substituted 2,2'-anhydrouridines. In: Tetrahedron. 1977 ; Vol. 33, No. 16. pp. 2131-2133.
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AB - 3',5'-Di-O-acetyl-2'-halogenouridines (1a, 1c and 1d) can be partially deacetylated at C-5' by transesterification with methanol-HCl, providing the 3'-O-acetyl derivatives 2a-2c. These can be converted into the 5'-O-mesyl derivatives 3a-3c, and latter into the 5'-chloro compounds 3d-3f. All 5'-substituted 2'-halogeno compounds give the corresponding 2,2'-anhydrouridine derivatives 4a-4c on treatment with NaOMe. Structures were proved by IR and 1H-NMR.

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