Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of purine and pyrimidine nucleobases.
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.
Kocalka
Petr
P
Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Praha 6, Czech Republic.
Pohl
Radek
R
Rejman
Dominik
D
Rosenberg
Ivan
I
D000970:Antineoplastic Agents / Q000494:pharmacology; D000998:Antiviral Agents / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D008293:Malates / Q000737:chemistry; D013058:Mass Spectrometry; D008956:Models, Chemical; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry; D011684:Purine Nucleosides / Q000737:chemistry; D011687:Purines / Q000737:chemistry*; D011741:Pyrimidine Nucleosides / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D008293:Malates; D009705:Nucleosides; D009711:Nucleotides; D011684:Purine Nucleosides; D011687:Purines; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines; D012997:Solvents; C030298:malic acid