Regiospecific synthesis of 6-halouridine derivatives: An effective method for coupling sterically hindered pyrimidine bases to ribose |
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| Authors: | Daniel J Blackburn Greggory T Kent Weiming Wu |
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| Institution: | Department of Chemistry and Biochemistry, San Francisco State University, San Francisco, CA 94132, USA |
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| Abstract: | 6-Halouridine derivatives were synthesized regiospecifically through the coupling of N3-protected 6-halouracil to a ribose derivative. The combination of the silylating reagent N,O-bis(trimethylsilyl)acetamide and Lewis acid catalyst trimethylsilyl trifluoromethanesulfonate is unique in their ability to facilitate the coupling of sterically hindered pyrimidine bases to ribose to form nucleoside derivatives. |
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| Keywords: | 6-Halouracil Nucleoside synthesis Ribosylation Pyrimidine silylation Sterically hindered pyrimidine |
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