Title: Efficient Synthesis of [2-<sup>15</sup>N]Guanosine and 2′-Deoxy[2′-<sup>15</sup>N]Guanosine Derivatives Using N-(<i>tert</i>-Butyldimethylsilyl)[<sup>15</sup>N]Phthalimide as a<sup>15</sup>N-Labeling Reagent
Abstract: Nucleophilic aromatic substitution of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-2-fluoro-9 H-purine with N-(tert-butyldimethylsilyl)[ 15 N]phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[ 15 N]phthalimidopurine derivative, which was subsequently converted to the [2-15N]guanosine derivative was also efficiently synthesized through a similar procedure. Keywords: Nucleosides bearing 15N-labeled exocyclic amino groups[2-15N]Guanosine2-Deoxy[2′15-N]guanosine Acknowledgments The authors thank Yasuo Shida for MS measurements and Chiseko Sakuma for the 15N NMR measurements, Analytical Center, Tokyo University of Pharmacy and Life Science. This work was supported by “High-Tech Reseach Center” Project for Private Universities: a matching fund subsidy from the Ministry of Education, Culture, Sports, Science, and Technology, 2002-2006. Notes a Reaction of 1a with non-labeled N-TBDMS-phthalimide. b The reaction was performed in the presence of Molecular Sieves 4 A (0.5 g/1 mmol of 1). The commercially available 1 M tetrabutylammonium fluoride (TBAF)/THF solution, containing H2O (∼5 wt.%), was added portionwise after drying over Molecular Sieves 3 A for 12 h. c Cesium fluoride (CsF) was added portionwise. d Non-labeled phthalimidopurine derivative.
Publication Year: 2006
Publication Date: 2006-01-01
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
Access and Citation
Cited By Count: 1
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot