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 asymet...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]<sub>D</sub><sup>20</sup>, IR, UV, <sup>1</sup>H NMR, <sup>13</sup>C 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.展开更多
基金Project supported by the National Natural Science Foundation of China (Grant No. 29672004)
文摘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]<sub>D</sub><sup>20</sup>, IR, UV, <sup>1</sup>H NMR, <sup>13</sup>C 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.
