335693-23-7Relevant articles and documents
A highly diastereoselective vinylogous Mannich condensation and 1,4-conjugate addition of (Z)-propenyl cuprate in the synthesis of an influenza neuraminidase inhibitor
Barnes, David M.,Bhagavatula, Lakshmi,DeMattei, John,Gupta, Ashok,Hill, David R.,Manna, Sukumar,McLaughlin, Maureen A.,Nichols, Paul,Premchandran, Ramiya,Rasmussen, Michael W.,Tian, Zhenping,Wittenberger, Steven J.
, p. 3541 - 3551 (2007/10/03)
A practical synthesis of neuraminidase influenza inhibitor, A-322278, has been developed. Asymmetry is introduced into the synthesis by an enzyme mediated ester hydrolysis. A highly diastereoselective vinylogous Mannich condensation reaction of N-Boc-2-te
Synthesis of an influenza neuraminidase inhibitor intermediate via a highly diastereoselective coupling reaction.
Barnes, David M,McLaughlin, Maureen A,Oie, Tetsuro,Rasmussen, Michael W,Stewart, Kent D,Wittenberger, Steven J
, p. 1427 - 1430 (2007/10/03)
[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.
