Solid phase synthesis of carbocyclic l-2'-deoxynucleosides

Org Lett. 2001 May 17;3(10):1471-3. doi: 10.1021/ol015783n.

Abstract

[reaction: see text] Carbocyclic L-2'deoxynucleosides 17 were synthesized on solid phase in four steps from the appropriately protected intermedate 11. The Mitsunobu reaction was used as a condensation method between the carbocyclic moiety and heterocyclic bases. The regioselectivity of the carbocyclic nucleosides was compared between the solid and solution phase syntheses.

Publication types

  • Comparative Study
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alanine / analogs & derivatives
  • Alanine / isolation & purification*
  • Alanine / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antiviral Agents / chemical synthesis
  • Bridged Bicyclo Compounds, Heterocyclic / isolation & purification*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
  • Combinatorial Chemistry Techniques / methods*
  • Nucleosides / chemical synthesis*
  • Solvents / pharmacology

Substances

  • Antineoplastic Agents
  • Antiviral Agents
  • Bridged Bicyclo Compounds, Heterocyclic
  • Nucleosides
  • Solvents
  • neodysiherbaine A
  • Alanine