Mechanism-Based Solution to the ProTide Synthesis Problem: Selective Access to Sofosbuvir, Acelarin, and INX-08189
| Autor: | Bryon Simmons, Steven M. Silverman, Zhuqing Liu, Artis Klapars, Ana Bellomo |
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| Rok vydání: | 2017 |
| Předmět: |
NUCLEOSIDE
Sofosbuvir 010405 organic chemistry Chemistry Otras Ciencias Químicas Organic Chemistry Ciencias Químicas Protide Mechanism based REGIOSELECTIVE 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences medicine Organic chemistry Stereoselectivity Physical and Theoretical Chemistry PHOSPHORYLATION Dimethylaluminum chloride CIENCIAS NATURALES Y EXACTAS medicine.drug |
| Zdroj: | Organic letters. 19(9) |
| ISSN: | 1523-7052 |
| Popis: | A general and efficient method for the synthesis of pronucleotide (ProTide) 5'-phosphoramidate monoesters is reported. This method consists of a highly stereoselective 5'-phosphorylation mediated by dimethylaluminum chloride to afford the desired target ProTides in excellent yields without employing 3'-protection strategies. The application of this methodology to the synthesis of a number of pharmaceutically relevant compounds currently marketed or under investigation in clinical research is demonstrated. Fil: Simmons, Bryon. Merck & Co.; Estados Unidos Fil: Liu, Zhuqing. Merck & Co.; Estados Unidos Fil: Klapars, Artis. Merck & Co.; Estados Unidos Fil: Bellomo Peraza, Ana Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias ; Argentina. Merck & Co.; Estados Unidos Fil: Silverman, Steven M.. Merck & Co.; Estados Unidos |
| Databáze: | OpenAIRE |
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