Synthesis of 9-[1-(substituted)-3-(phosphonomethoxy)propyl]adenine derivatives as possible antiviral agents |
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Authors: | Wu Minwan El-Kattan Yahya Lin Tsu-Hsing Ghosh Ajit Vadlakonda Satish Kotian Pravin L Babu Yarlagadda S Chand Pooran |
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Institution: | BioCryst Pharmaceuticals inc., Birmingham, Alabama 35244, USA. |
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Abstract: | Acyclic N9 adenine nucleosides substituted at C-1' position were prepared by the Mitsunobu reaction of 1-tert-butyldimethylsilyl-4-pivaloylbutan-1,2,4-triol (5) with adenine. Pivaloyl hydroxyl was modified to the phosphonomethoxy derivatives, and the tert-butyldimethylsilyl hydroxyl was converted to methoxy, azido, amino, fluoro, and c-hydroxyethyl and was eliminated to give vinyl. The resulting phosphonic acids were converted to prodrugs also. |
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