title: Practical synthesis of a potent hepatitis C virus RNA replication inhibitor.
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.
authors.affiliation: Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. matthew_bio@merck.com
authors.forename: Matthew M
authors.initials: MM
authors.lastname: Bio
authors.forename: Feng
authors.initials: F
authors.lastname: Xu
authors.forename: Marjorie
authors.initials: M
authors.lastname: Waters
authors.forename: J Michael
authors.initials: JM
authors.lastname: Williams
authors.forename: Kimberly A
authors.initials: KA
authors.lastname: Savary
authors.forename: Cameron J
authors.initials: CJ
authors.lastname: Cowden
authors.forename: Chunhua
authors.initials: C
authors.lastname: Yang
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Buck
authors.forename: Zhiguo J
authors.initials: ZJ
authors.lastname: Song
authors.forename: David M
authors.initials: DM
authors.lastname: Tschaen
authors.forename: R P
authors.initials: RP
authors.lastname: Volante
authors.forename: Robert A
authors.initials: RA
authors.lastname: Reamer
authors.forename: Edward J J
authors.initials: EJ
authors.lastname: Grabowski
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D016174:Hepacivirus / Q000235:genetics*; D009682:Magnetic Resonance Spectroscopy; D012367:RNA, Viral / Q000096:biosynthesis*
chemical_list: D000998:Antiviral Agents; D012367:RNA, Viral