title: Synthesis of an influenza neuraminidase inhibitor intermediate via a highly diastereoselective coupling reaction.
abstract: [reaction: see text]. A highly diastereoselective coupling reaction between TBSOP (3) and trityl sulfenimine 4 was developed which provided influenza neuraminidase inhibitor intermediate 7 in 80% yield and >99% de after crystallization. The reaction was shown to be reversible with the high diastereoselectivity resulting from a favorable H-bonding interaction in the major diastereomer.
authors.affiliation: Global Pharmaceutical R&D, Process Research & Development, Abbott Laboratories, 1401 Sheridan Road, D-R450, Bldg. R8, North Chicago, Illinois 60064-4000, USA.
authors.forename: David M
authors.initials: DM
authors.lastname: Barnes
authors.forename: Maureen A
authors.initials: MA
authors.lastname: McLaughlin
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Oie
authors.forename: Michael W
authors.initials: MW
authors.lastname: Rasmussen
authors.forename: Kent D
authors.initials: KD
authors.lastname: Stewart
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Wittenberger
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000201:enzymology*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: C456059:A 315675; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D011759:Pyrrolidines; D009439:Neuraminidase