化学稳定的2-（三甲基硅基）苯甲酰基酰化的核苷衍生物的合成与性质

Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group.

作者信息

Yamada Ken, Taguchi Haruhiko, Ohkubo Akihiro, Seio Kohji, Sekine Mitsuo

机构信息

Department of Life Science, Tokyo Institute of Technology, Japan.

出版信息

Bioorg Med Chem. 2009 Aug 15;17(16):5928-32. doi: 10.1016/j.bmc.2009.07.003. Epub 2009 Jul 7.

DOI:10.1016/j.bmc.2009.07.003

PMID:19632121

Abstract

We report the synthesis and properties of nucleoside derivatives acylated by 2-(trimethylsilyl)benzoyl (TMSBz) that proved to be extremely stable under basic conditions when introduced into the 5'-hydroxyl group of thymidine, the 4-amino group of deoxycytidine and the 2'-hydroxyl group of uridine. In particular, 2'-O-TMSBz-uridine could be isolated and was more stable in pyridine, while it isomerized in CH(2)Cl(2) in the presence of Et(3)N to yield a mixture of the 2'-O- and 3'-O-acylated species.

摘要

我们报道了用2-(三甲基硅基)苯甲酰基（TMSBz）酰化的核苷衍生物的合成及性质。当将其引入胸腺嘧啶核苷的5'-羟基、脱氧胞苷的4-氨基和尿苷的2'-羟基时，这些衍生物在碱性条件下表现出极高的稳定性。特别是，2'-O-TMSBz-尿苷可以被分离出来，并且在吡啶中更稳定，而在二氯甲烷中，在三乙胺存在的情况下会发生异构化，生成2'-O-和3'-O-酰化产物的混合物。