Synthesis of novel chiral compounds of purine and pyrimidine bases

The physiologically active groups such as purine and pyrimidine bases are introduced to the asymmetric ynthesis. The optically pure compounds bearing purine and pyrimidine bases （5a—5e） were prepared via the asymetric Michael addition reaction of purines and pyrimidines as Michael donators with the chiral source 5-（R）-[（1R, 2S, 5R）-menthyloxy]-2（5H）-furanone （3a）, which was prepared from the natural chiral auxiliary （-）-menthol. The synthetic method was studied in detail and the new compounds were identified on the basis of their analytical data and spectroscopic data, such as [α]D20, IR, UV, 1H NMR, 13C NMR and MS. The absolute configuration of 5a was established by X-ray crystallography. The results provided an efficient synthetic route to chiral purines and pyrimidine analogues, and offered chiral sources for further research on the physiologically active compounds of chiral nucleotides.

The physiologically active groups such as purine and pyrimidine bases are introduced to the asymmetric synthesis. The optically pure compounds bearing purine and pyrimidine bases (5a—5e) were prepared via the asymmetric Michael addition reaction of purines and pyrimidines as Michael donators with the chiral source 5-(R)-[(lR, 2S, 5R)-menthyloxy]-2(5H)-furanone (3a), which was prepared from the natural chiral auxiliary (-)-menthol. The synthetic method was studied in detail and the new compounds were identified on the basis of their analytical data and spectroscopic data, such as [α] D 20 , IR, UV,1H NMR,13C NMR and MS. The absolute configuration of5a was established by X-ray crystallography. The results provided an efficient synthetic route to chiral purines and pyrimidine analogues, and offered chiral sources for further research on the physiologically active compounds of chiral nucleotides.