The acidic hydrolysis of: N -acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)

Paola Rota; Paolo La Rocca; Federica Cirillo; Marco Piccoli; Pietro Allevi; Luigi Anastasia

doi:10.1039/c9ra10215a

The acidic hydrolysis of: N -acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)

Paola Rota, Paolo La Rocca, Federica Cirillo, Marco Piccoli, Pietro Allevi, Luigi Anastasia

Research output: Contribution to journal › Article › peer-review

Abstract

The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline affords the corresponding 2,3-unsaturated amino ester, which was not previously detected (nor isolated) due to the unexpected rearrangement into its corresponding alcohol. In this work, we unveiled the mechanism of these reactions and optimized the conditions to obtain either synthetic intermediate.

Original language	English
Pages (from-to)	162-165
Number of pages	4
Journal	RSC Advances
Volume	10
Issue number	1
DOIs	https://doi.org/10.1039/c9ra10215a
Publication status	Published - Jan 1 2019

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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abstract = "The acidic hydrolysis of N-acetylneuraminic 4,5-oxazoline affords the corresponding 2,3-unsaturated amino ester, which was not previously detected (nor isolated) due to the unexpected rearrangement into its corresponding alcohol. In this work, we unveiled the mechanism of these reactions and optimized the conditions to obtain either synthetic intermediate.",

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AU - Piccoli, Marco

AU - Allevi, Pietro

AU - Anastasia, Luigi

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The acidic hydrolysis of: N -acetylneuraminic 4,5-oxazoline allows a direct functionalization of the C5 position of Neu5Ac2en (DANA)

Abstract

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