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

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.

• Authors: Evan J Horn, Jacquelyn Gervay-Hague
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 74 Issue 11 Pg. 4357-9 (Jun 05 2009) ISSN: 1520-6904 [Electronic] United States
• PMID: 19413276 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Antiviral Agents
• Enzyme Inhibitors
• 2-deoxy-2,3-dehydro-N-acetylneuraminic acid
• Neuraminidase
• N-Acetylneuraminic Acid
• Zanamivir

Topics

• Acetylation
• Antiviral Agents
• Enzyme Inhibitors (chemistry)
• Heating
• Methods
• N-Acetylneuraminic Acid (analogs & derivatives, chemistry)
• Neuraminidase (antagonists & inhibitors)
• Organic Chemistry Phenomena
• Vacuum
• Zanamivir