Practical synthesis of a potent hepatitis C virus RNA replication inhibitor

ORGN 522

Feng Xu1, Marjorie Waters2, Matthew M. Bio1, Kimberly Savary1, Cameron Cowden1, Chunhua Yang1, Robert A. Reamer1, Elizabeth Buck1, Zhiguo Song2, J. Michael Williams1, David Tschaen2, Ralph P. Volante1, Edward J. J. Grabowski1, and Richard Tillyer1. (1) Process Research, Merck & Co., Inc, PO Box 2000, Rahway, NJ 07065, (2) Process Research, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065
A practical synthesis of a potent hepatitis C virus RNA replication inhibitor is described. Starting with inexpensive diacetone glucose, the 12-step synthesis features 1) a novel stereoselective rearrangement to prepare the key crystalline furanose diol and 2) a highly selective glycosylation to couple the C-2 branched furanose epoxide with deazapurine.