Novel TSAO derivatives modified at positions 3" and 4" of the spiro moiety

Nucleosides Nucleotides. 1999 Apr-May;18(4-5):675-6. doi: 10.1080/15257779908041536.

Abstract

We have explored the introduction of different functional groups at positions 3" and 4" of the spiro moiety of TSAO-T. Alkylation of this spiro moiety afforded mixtures of N and/or C-alkylated derivatives, while acylation occurs, exclusively, on the amino group. Position 3" has been selectively functionalized by halogenation followed by Stille-cross coupling reaction with organostannanes under a variety of experimental conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Spiro Compounds / chemistry*
  • Thymidine / analogs & derivatives*
  • Thymidine / chemistry
  • Uridine / analogs & derivatives

Substances

  • Spiro Compounds
  • 1-(2',5'-bis-O-(tert-butyldimethylsilylribofuranosyl)-3-N-methylthymine)-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
  • Thymidine
  • TSAO-T
  • Uridine