The first isolation of an alkoxy-N,N-dialkylaminodifluorosulfane from the reaction of an alcohol and DAST: an efficient synthesis of (2S,3R,6S)-3-fluoro-2,6-diaminopimelic acid

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Andrew Sutherland and John C. Vederas


Abstract

During improvement of the synthesis of (2S,3R,6S)-3-fluoro-2,6-diaminopimelic acid 3, a potent inhibitor of DAP epimerase, a stable alkoxy-N,N-dialkylaminodifluorosulfane 9 was isolated from the reaction of alcohol 6 with DAST


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