Straightforward access to 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid

Paola Rota; Paolo La Rocca; Valentina Franco; Pietro Allevi

doi:10.1016/j.tet.2020.131699

Straightforward access to 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid

Paola Rota, Paolo La Rocca, Valentina Franco, Pietro Allevi

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

Abstract

The facile syntheses of previously unreported 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid are herein described. The procedure involves a ring-opening of the 4,5-oxazoline of N-acetylneuraminic acid, the acylation of the intermediate free amine, its conversion into the 4,5-oxazoline of N-glycolylneuraminic acid and the subsequent Ferrier reaction or C4 nucleophilic substitution.

Original language	English
Article number	131699
Journal	Tetrahedron
Volume	76
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2020.131699
Publication status	Published - Dec 4 2021

Keywords

Ferrier reaction
Glycals
N-Glycolylneuraminic acid
Oxazoline of sialic acid
Sialidase inhibitor

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2020.131699

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title = "Straightforward access to 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid",

abstract = "The facile syntheses of previously unreported 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid are herein described. The procedure involves a ring-opening of the 4,5-oxazoline of N-acetylneuraminic acid, the acylation of the intermediate free amine, its conversion into the 4,5-oxazoline of N-glycolylneuraminic acid and the subsequent Ferrier reaction or C4 nucleophilic substitution.",

keywords = "Ferrier reaction, Glycals, N-Glycolylneuraminic acid, Oxazoline of sialic acid, Sialidase inhibitor",

author = "Paola Rota and {La Rocca}, Paolo and Valentina Franco and Pietro Allevi",

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T1 - Straightforward access to 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid

AU - Rota, Paola

AU - La Rocca, Paolo

AU - Franco, Valentina

AU - Allevi, Pietro

PY - 2021/12/4

Y1 - 2021/12/4

N2 - The facile syntheses of previously unreported 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid are herein described. The procedure involves a ring-opening of the 4,5-oxazoline of N-acetylneuraminic acid, the acylation of the intermediate free amine, its conversion into the 4,5-oxazoline of N-glycolylneuraminic acid and the subsequent Ferrier reaction or C4 nucleophilic substitution.

AB - The facile syntheses of previously unreported 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid are herein described. The procedure involves a ring-opening of the 4,5-oxazoline of N-acetylneuraminic acid, the acylation of the intermediate free amine, its conversion into the 4,5-oxazoline of N-glycolylneuraminic acid and the subsequent Ferrier reaction or C4 nucleophilic substitution.

KW - Ferrier reaction

KW - Glycals

KW - N-Glycolylneuraminic acid

KW - Oxazoline of sialic acid

KW - Sialidase inhibitor

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DO - 10.1016/j.tet.2020.131699

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VL - 76

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 49

M1 - 131699

ER -

Straightforward access to 2,3- and 3,4-unsaturated derivatives of N-glycolylneuraminic acid

Abstract

Keywords

ASJC Scopus subject areas

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