Practical synthesis of a potent hepatitis C virus RNA replication inhibitor

…, F Xu, M Waters, JM Williams, KA Savary…

Index: Bio, Matthew M.; Xu, Feng; Waters, Marjorie; Williams, J. Michael; Savary, Kimberly A.; Cowden, Cameron J.; Yang, Chunhua; Buck, Elizabeth; Song, Zhiguo J.; Tschaen, David M.; Volante; Reamer, Robert A.; Grabowski, Edward J. J. Journal of Organic Chemistry, 2004 , vol. 69, # 19 p. 6257 - 6266

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Citation Number: 59

Abstract

A practical, efficient synthesis of 1, a hepatitis C virus RNA replication inhibitor, is described. Starting with the inexpensive diacetone glucose, the 12-step synthesis features a novel stereoselective rearrangement to prepare the key crystalline furanose diol intermediate. This is followed by a highly selective glycosidation to couple the C-2 branched furanose epoxide with deazapurine.