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Evan Horn

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Organization: University of California
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Efficient Method for the Preparation of Peracetylated Neu5Ac2en by Flash Vacuum Pyrolysis
Co-reporter:Evan J. Horn and Jacquelyn Gervay-Hague
The Journal of Organic Chemistry 2009 Volume 74(Issue 11) pp:4357-4359
Publication Date(Web):May 4, 2009
DOI:10.1021/jo900224t
Peracetylated Neu5Ac2en methyl ester, an intermediate in the synthesis of the influenza neuraminidase inhibitor Relenza, has been synthesized in high yields from peracetylated Neu5Ac methyl ester by flash vacuum pyrolysis. Mechanistic evidence including deuterium labeled studies and DFT (B3LYP) calculations suggest this transformation proceeds via an intramolecular syn-elimination.
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