Synthesis of D-altritol nucleosides with a 3'-O-tert-butyldimethylsilyl protecting group

Nucleosides Nucleotides Nucleic Acids. 2004;23(1-2):439-55. doi: 10.1081/ncn-120028338.

Abstract

Four D-altritol nucleosides with a 3'-O-tert-butyldimethylsilyl protecting group are synthesized (base moieties are adenine, guanine, thymine and 5-methylcytosine). The nucleosides are obtained by ring opening reaction of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol. Optimal reaction circumstances (NaH, LiH, DBU, phase transfer, microwave irridation) for the introduction of the heterocycles are base-specific. For the introduction of the 3'-O-silyl protecting group, long reaction times and several equivalents of tert-butyldimethylsilyl chloride are needed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Nucleosides / chemical synthesis*
  • Silanes / chemical synthesis*
  • Sugar Alcohols / chemical synthesis*

Substances

  • Nucleosides
  • Silanes
  • Sugar Alcohols
  • altritol