Synthesis of N2-substituted deoxyguanosine nucleosides from 2-fluoro-6-O-(trimethylsilylethyl)-2'-deoxyinosine.
Syntheses of N2-substituted nucleosides have been studied for many years, primarily with ribonucleosides. However, the primary route to these compounds requires acidic conditions that are too vigorous for the acid-labile deoxyribonucleosides. The current strategy takes advantage of methods for low-temperature, nonaqueous diazotization of ribosides in organic solvents using t-butyl nitrate as the diazotizing agent and HF/pyridine as the fluoride source for the preparation of a 2-fluoro-2-deoxyinosine derivative that can be used to synthesize N2-substituted deoxyguanosine.
Harris
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Vanderbilt University, Nashville, Tennessee, USA.
Harris
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D001671:Biochemistry / Q000379:methods*; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007288:Inosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009584:Nitrogen; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
C528723:2-fluoro-6-O-(trimethylsilylethyl)-2'-deoxyinosine; D014297:Trimethylsilyl Compounds; D007288:Inosine; D003849:Deoxyguanosine; C012271:deoxyinosine; D009584:Nitrogen