ORGN 454 |
| Daniel Hutter and Steven A Benner. Department of Chemistry, University of Florida, Gainesville, FL 32611-7200 |
| The synthesis of nucleoside 5'-triphosphates is usually tedious and low yielding, involving several steps of protection and deprotection. We have developed a short and high yielding route to synthesize 5'-triphosphates directly from the unprotected nucleosides. Our approach is based on the chemoselective reaction of a sterically demanding chlorophosphite with the primary 5'-hydroxyl of the nucleoside, as well as on the stability of the resulting phosphites which allows for their purification by column chromatography. These properties lead to the high yielding synthesis of pure 5'-phosphite which can then be converted to the triphosphate via substitution by pyrophosphate and subsequent oxidation. The synthesis of the hindered chlorophosphite will be described as well. |
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Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |