Efficient synthesis of antiviral agent uprifosbuvir enabled by new synthetic methods
An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis was achieved by development of several synthetic methods: (1) complexation-driven selective acyl migration/oxidation; (2) BSA-mediated cycli...
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| Published in | Chemical science (Cambridge) Vol. 12; no. 26; pp. 931 - 936 |
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| Main Authors | , , , , , , , , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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CAMBRIDGE
Royal Soc Chemistry
07.07.2021
Royal Society of Chemistry The Royal Society of Chemistry |
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| Abstract | An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis was achieved by development of several synthetic methods: (1) complexation-driven selective acyl migration/oxidation; (2) BSA-mediated cyclization to anhydrouridine; (3) hydrochlorination using FeCl
3
/TMDSO; (4) dynamic stereoselective phosphoramidation using a chiral nucleophilic catalyst. The new route improves the yield of uprifosbuvir 50-fold over the previous manufacturing process and expands the tool set available for synthesis of antiviral nucleotides.
An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. |
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| AbstractList | An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis was achieved by development of several synthetic methods: (1) complexation-driven selective acyl migration/oxidation; (2) BSA-mediated cyclization to anhydrouridine; (3) hydrochlorination using FeCl
3
/TMDSO; (4) dynamic stereoselective phosphoramidation using a chiral nucleophilic catalyst. The new route improves the yield of uprifosbuvir 50-fold over the previous manufacturing process and expands the tool set available for synthesis of antiviral nucleotides. An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis was achieved by development of several synthetic methods: (1) complexation-driven selective acyl migration/oxidation; (2) BSA-mediated cyclization to anhydrouridine; (3) hydrochlorination using FeCl 3 /TMDSO; (4) dynamic stereoselective phosphoramidation using a chiral nucleophilic catalyst. The new route improves the yield of uprifosbuvir 50-fold over the previous manufacturing process and expands the tool set available for synthesis of antiviral nucleotides. An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis was achieved by development of several synthetic methods: (1) complexation-driven selective acyl migration/oxidation; (2) BSA-mediated cyclization to anhydrouridine; (3) hydrochlorination using FeCl3/TMDSO; (4) dynamic stereoselective phosphoramidation using a chiral nucleophilic catalyst. The new route improves the yield of uprifosbuvir 50-fold over the previous manufacturing process and expands the tool set available for synthesis of antiviral nucleotides. |
| Author | Limanto, John Liu, Guiquan Song, Zhiguo Jake Kassim, Amude M Maligres, Peter E Zultanski, Susan L Calabria, Ralph Larsen, Mona Utne Wright, Timothy J Chen, Wenyong Ruck, Rebecca T Tan, Lushi Klapars, Artis Hyde, Alan M Campeau, Louis-Charles Davis, Tyler A DiRocco, Daniel A Shevlin, Michael Moment, Aaron Peng, Feng Simmons, Bryon L Chung, John Y. L Dalby, Stephen M Campos, Kevin R |
| AuthorAffiliation | Merck & Co., Inc Department of Process Research and Development WuXi STA |
| AuthorAffiliation_xml | – name: Merck & Co., Inc – name: Department of Process Research and Development – name: WuXi STA |
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| Snippet | An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Ferric chloride Hydrochlorination Nucleotides Oxidation Physical Sciences Science & Technology Stereoselectivity Synthesis |
| Title | Efficient synthesis of antiviral agent uprifosbuvir enabled by new synthetic methods |
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