New 7-trifluoromethyl-7-deazapurine ribonucleoside analogs (1a-c) and their protides (2a-c) were successfully synthesized from riborlactol and 1-a-bromo-ribose derivatives using Silyl-Hilbert-Johnson or nucleobase-anion substitution reaction and then aromatic trifluoromethyl substitution as key step reactions. The b-selective glycosylation reaction of the benzyloxonium ribose, or 1-a-bromo-ribose intermediates with persilylated 6-chloro-7-iodo-7-deazapurine , or anionized compound, followed by the aromatic trifluoromethylation reaction with MFSDA and CuI and then treatment with ammonia afforded 7-trifluoromethyl-7-deazapurine ribonucleosides (1a-c) in excellent yield, which were converted into their phosphoramidate prodrugs (2a-c) employing chlorophosphoramide derivative. Unfortunately, none of them showed any marked anti-HCV, anti-Zika and anti-Ebola activities.

Efficient synthetic methods of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their phosphoramidate prodrugs

2019 Spring National Meeting

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