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

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)4357-4359
Number of pages3
JournalJournal of Organic Chemistry
Volume74
Issue number11
DOIs
StatePublished - Jun 5 2009

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Esters
Pyrolysis
Zanamivir
Vacuum
Deuterium
Neuraminidase
Discrete Fourier transforms
2-deoxy-2,3-dehydro-N-acetylneuraminic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis. / Horn, Evan J.; Gervay-Hague, Jacquelyn.

In: Journal of Organic Chemistry, Vol. 74, No. 11, 05.06.2009, p. 4357-4359.

Research output: Contribution to journalArticle

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