Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 24, Issue 9, Pages 1772-1777Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.0c00310
Keywords
diisopropylamine; C-glycosylation; remdesivir; COVID-19
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Funding
- National Science and Technology Major Projects for Major New Drugs Innovation and Development [2018ZX09711003, 2020YFC0841700]
- National Natural Science Foundation of China [21921002, 21991114]
- Special Funds for Prevention and Control of COVID-19 of Sichuan University
- Chengdu Municipal Science and Technology Bureau [2020-YF08-00002-GX]
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The bulk supply of the antiviral C-nucleoside analogue remdesivir is largely hampered by a low-yielding Cglycosylation step in which the base is coupled to the pentose unit. Here, we disclose a significantly improved methodology for this critical transformation. By utilizing diisopropylamine as a cost-effective additive, the addition reaction furnishes an optimal yield of 75% of the desired ribofuranoside adduct, representing the highest yield obtained thus far for this key step. The method proved suitable for hectogram scale synthesis without column chromatographic operations.
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