Large scale synthesis of 2′-Amino-LNA thymine and 5-methylcytosine nucleosides

Andreas Stahl Madsen, Anna Sondergaard Jorgensen, Troels Bundgaard Jensen, Jesper Wengel, Andreas Stahl Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Thymine intermediate 17 has been synthesized on a multigram scale (50 g, 70 mmol) from starting sugar 1 in 15 steps in an overall yield of 73%, with only 5 purification steps. The key thymine intermediate 18 was obtained from 17 in a single step in 96% yield, whereas the key 5-methylcytosine intermediate 20 was obtained from 17 in 2 steps in 58% yield. This highly efficient large scale route necessitates only 2 and 3 novel steps to obtain N2′-functionalized thymine and 5-methylcytosine amino-LNA phosphoramidites from these key intermediates, respectively. © 2012 American Chemical Society.
Original languageEnglish
JournalJournal of Organic Chemistry
Volume77
Issue number23
Pages (from-to)10718-10728
ISSN0022-3263
DOIs
Publication statusPublished - 2012

Keywords

  • Chemistry
  • Organic compounds

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