Regioselective synthesis of 13C1-labeled 2-deoxyribonolactones

Michael P. Hayes, Paul J. Hatala, Brian A. Sherer, Xiaohong Tong, Nilo Zanatta, Philip N Borer, James Kallmerten

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Syntheses of the five regioselectively 13C1-labeled 5-O-benzyl-2-deoxyribonolactones are described. 13C1-Labeled deoxyribonolactones were prepared by addition of KCN to epoxides 7 and subsequent lactonization of the resulting nitriles. Integration of the independent schemes leading to the five isotopomers of 9 results in an efficient and cost effective preparation of labeled mixtures of 13C mono-labeled deoxyribonolactones. These mixtures are the pivotal intermediates in the preparation of 'population labeled' 13C-labeled nucleoside phosphoramidites for solid-phase oligonucleotide synthesis.

Original languageEnglish (US)
Pages (from-to)1515-1524
Number of pages10
JournalTetrahedron
Volume57
Issue number8
DOIs
StatePublished - Feb 18 2001

Keywords

  • Labeling
  • NMR
  • Nucleic acids
  • Regioselection

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Hayes, M. P., Hatala, P. J., Sherer, B. A., Tong, X., Zanatta, N., Borer, P. N., & Kallmerten, J. (2001). Regioselective synthesis of 13C1-labeled 2-deoxyribonolactones. Tetrahedron, 57(8), 1515-1524. https://doi.org/10.1016/S0040-4020(00)01148-0