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Synthesis of an influenza neuraminidase inhibitor intermediate via a highly diastereoselective coupling reaction
Authors:Barnes David M  McLaughlin Maureen A  Oie Tetsuro  Rasmussen Michael W  Stewart Kent D  Wittenberger Steven J
Institution:Global Pharmaceutical R&D, Process Research & Development, Abbott Laboratories, 1401 Sheridan Road, D-R450, Bldg. R8, North Chicago, Illinois 60064-4000, USA.
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.
Keywords:
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