【作者】 李乾坤；

【导师】 蒋忠良；

【作者基本信息】 同济大学 ， 有机化学， 2007， 硕士

【摘要】 杯芳烃是一类由苯酚和甲醛缩合而成的大环化合物，由于杯芳烃的上沿和下沿容易进行化学修饰及其本身具有一个大小可调节的疏水空腔，使得杯芳烃对客体分子表现出特殊的识别能力。因此杯芳烃作为继冠醚、环糊精之后的第三代人工合成受体分子已在分子识别和自组装研究方面取得了重要进展并显示了广泛的应用前景，目前越来越多的文献报道了将核苷酸的碱基或核苷基通过化学为法接到各种大分子化合物的母体上去，用来作为另一个相应的核苷酸位置的“识别子”。 课题设计了两种未见文献报道的含有核苷基团的新型杯芳烃的衍生物-目标产物A和B，由于带有核苷以及肽键，希望可以利用核苷碱基之间的相互识别作用以及肽键对于-COOH和-NH₂的识别作用作为分子识别因子，因此对于分子的识别和自组装具有更大的意义。 目标产物的母体结构是杯芳烃下沿部分利用溴乙酸乙酯修饰的产物，而侧链是使用尿苷为原料经过丙叉保护、磺酰化、叠氮化、还原四步反应得来，我们通过一系列的条件试验，不断优化实验条件和实验路线，最终找到了最佳的方案合成出我们的目标化合物。更多还原

【Abstract】 Calixarenes, the synthetic macrocycles derived from the condensation of phenols and formaldehyde, display recognition abilities to many guest molecules including those having biological activity on account of their hydrophobic cavities and are easily modified at the lower-rim or the upper-rim. Calixarenes taken as the third general artificial synthetic receptors, following crown ethers and cyclodextrins, have been well explored in molecular recognition and molecular self-assembly. At present, more and more literatures have reported linking nucleoside group or the nucleoside basic group to macromolecular compounds, as the recognized point of the position of another nucleoside group.In this paper, we designed two new derivatives of calix[4]arene containing nucleoside those have no literature reported. Because of nucleoside and peptide linkage, we hope we can use the recognition between the nucleosids and between -COOH 和-NH₂ as the recognized point. It has a bigger significance in molecular recognition and molecular self-assembly.Calix[4]arene is modified at the lower-rim with bromoacetate to form the main structure of the target compound, and with Uridine as the starting material, the side chain was synthesiszed by means of the protection of acetone, sulphonylation, azidation and reduction. We did lots of experimental to optimize the condition and the synthesis methods, and finally found the best plan to synthesize our target compound.更多还原