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Enantioselective synthesis of both enantiomers of 2-amino-6-phosphonohexanoic acid [(R)- and (S)-AP6], a potent and specific agonist of AMPA receptor subtype

✍ Scribed by Oscar García-Barradas; Eusebio Juaristi

Book ID: 104361183
Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 226 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00162-6

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✦ Synopsis

The preparation of both enantiomers of 2-amino-6-phosphonohexanoic acid [(R)-and (S)-AP6] is described. The highly diastereoselective alkylation of imidazolidinones 4 and hydrolysis of the alkylated products [(2R,5R, l'S)-6 and (2S,5S,1'S)-6] proceeds under relatively mild conditions to give the physiologically important, enantiopure aminophosphonic acids (R)-AP6 and (S)-AP6.

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