Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group
Ken Yamada1, Haruhiko Taguchi, Akihiro Ohkubo
1Department of Life Science, Tokyo Institute of Technology, Japan.
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.
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