Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group.
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.
Yamada
Ken
K
Department of Life Science, Tokyo Institute of Technology, Japan.
Taguchi
Haruhiko
H
Ohkubo
Akihiro
A
Seio
Kohji
K
Sekine
Mitsuo
M
D001565:Benzoates / Q000737:chemistry*; D007536:Isomerism; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
C541624:2-(trimethylsilyl)benzoic acid; D001565:Benzoates; D009705:Nucleosides; D014297:Trimethylsilyl Compounds; D013936:Thymidine; D014529:Uridine