SYNTHESIS OF RACEMIC AND ENANTIOMERIC 3-PYRROLIDINYL DERIVATIVES OF PURINE AND PYRIMIDINE NUCLEOBASES

Abstract

The present work relates to the synthesis of pyrrolidine nucleoside analogs. Starting from malic acid, we have elaborated a high-yield synthesis of racemic and enantiomeric N-protected 3-pyrrolidinols and their O-mesyl derivatives as key compounds for alkylations of purine and pyrimidine nucleobases. On varying base and solvent, we have found conditions providing both satisfactory N-/O-regioisomeric ratio and acceptable yield for pyrimidine compounds.

Keywords:

• N-Protected 3-Pyrrolidinols
• Pyrimidines
• Purines
• O,N-Alkylation
• Pyrrolidine Nucleosides