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J Org Chem. 2009 Jun 5;74(11):4357-9. doi: 10.1021/jo900224t.

Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis.

Author information

1
Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, California 95616, USA. horne@uci.edu

Abstract

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.

PMID:
19413276
PMCID:
PMC4557971
DOI:
10.1021/jo900224t
[Indexed for MEDLINE]
Free PMC Article

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