Adamska Ewelina, Barciszewski Jan, Markiewicz Wojciech T
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland.
Nucleosides Nucleotides Nucleic Acids. 2012;31(12):861-71. doi: 10.1080/15257770.2012.742198.
Convenient and efficient methods of the synthesis of N(6)- and N(4)-substituted derivatives of adenine and cytosine and their 2'-deoxyribosides were developed. The reactions of either unprotected nucleobases (adenine, cytosine) or unprotected 2'-deoxyribosides with aryl or alkyl aldehydes give corresponding Schiff bases that can be reduced to the target title compounds with high overall yields. In the case of aryl aldehydes the imine derivatives are obtained in the presence of methoxides in methanol and reduced with sodium borohydride. The corresponding reactions with alkyl aldehydes require the use of acetic acid and borane dimethyl sulfide complex instead.
开发了合成腺嘌呤和胞嘧啶的N(6)-和N(4)-取代衍生物及其2'-脱氧核糖苷的便捷高效方法。未保护的核碱基（腺嘌呤、胞嘧啶）或未保护的2'-脱氧核糖苷与芳基或烷基醛的反应生成相应的席夫碱，这些席夫碱可以被还原为目标标题化合物，总收率很高。对于芳基醛，亚胺衍生物在甲醇中的甲醇盐存在下获得，并用硼氢化钠还原。与烷基醛的相应反应则需要使用乙酸和硼烷二甲硫醚络合物代替。
