嘌呤、嘧啶类新手性化合物的合成

把具有生理活性的嘌呤、嘧啶类有机碱基引入不对称合成 ,利用嘌呤、嘧啶类化合物作为Michael加成给体与天然手性助剂 ( - ) 薄荷醇所制得的手性源 5 (R) [( 1R ,2S ,5R) 氧基 ] 2 ( 5H) 呋喃酮 ( 3a)进行不对称Michael加成反应 ,合成了新的光学纯嘌呤、嘧啶类手性化合物 ( 5a～ 5e) .详细地研究了合成方法并测定了它们的[α],IR ,UV ,1HNMR ,13 CNMR ,MS ,元素分析等结构分析数据 .经X 四圆衍射确定了腺嘌呤手性化合物 5a的立体化学结构 .为合成嘌呤、嘧啶类手性化合物提供了有效的途径 ,为深入研究具有生理活性的手性核苷酸类化合物提供了重要的手性源     

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]_D~(20), IR, UV, ~1H NMR, ~(13)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.