Highly stereoselective synthesis of (2'R)-[2'-2H]-deoxyribonucleosides and synthesis of their oligonucleotides

Nucleic Acids Symp Ser. 1992:(27):81-2.

Abstract

Highly stereoselective synthesis of (2'R)-[2'-2H]-2'-deoxyribonucleosides (2'R:2'S = > 99:1) were accomplished by treating 2'-bromo-3',5'-O-TPDS-2'-deoxyribonucleosides with tributyltin deuteride at lower temperatures such as -60 degrees C in the presence of triethylborane. Moreover, synthesis of some oligodeoxyribonucleosides involving them will be described.

MeSH terms

  • Boranes / chemistry
  • Deoxyribonucleosides / chemical synthesis*
  • Oligonucleotides / chemical synthesis*
  • Stereoisomerism
  • Trialkyltin Compounds / chemistry

Substances

  • Boranes
  • Deoxyribonucleosides
  • Oligonucleotides
  • Trialkyltin Compounds
  • tributyltin
  • triethylborane