ChemInform Abstract: A Regio- and Stereoselective Introduction of Azide at C-4 of 2,3- Unsaturated N-Acetylneuraminic Acids.
β Scribed by G. B. KOK; M. VON ITZSTEIN
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 28 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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Chemoenzymatic Synthesis of an N-Acetylneuraminic Acid Analogue Having a Carbamoylmethyl Group at C-4 as an Inhibitor of Sialidase from Influenza Virus. -The synthetic strategy for the preparation of the title analogue (XVI) requires the key intermediate (XII) which is synthesized by the Neu5Ac aldo
## Abstract The peracetylated methyl ester 1 of Nβacetylneuraminic acid was transformed into the oxazoline derivative 2, which was hydrogenated with Pd/C/H~2~ to give the 4βdeoxyβNeu5Ac2en derivative 3. Acid cleavage of the oxazoline 2 by trifluoroacetic acid (THF) gave the 4βepiβNeu5Ac2en derivati
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C-3 Acetoxylation of N-Acyl-2,3-dihydro-4-pyridones. -Stereoselective C-3 acetoxylation of various N-acyldihydropyridones (I) is achieved under mild conditions using lead tetraacetate. The analogous reaction of the indolizidinone (IV) to the cis product proceeds with considerably lower yield.