The first synthesis of N-acetylneuraminic acid 1,7-lactone

Raffaele Colombo; Mario Anastasia; Paola Rota; Pietro Allevi

doi:10.1039/b810447f

The first synthesis of N-acetylneuraminic acid 1,7-lactone

Chem Commun (Camb). 2008 Nov 21:(43):5517-9. doi: 10.1039/b810447f. Epub 2008 Sep 23.

Authors

Raffaele Colombo¹, Mario Anastasia, Paola Rota, Pietro Allevi

Affiliation

¹ Department of Chemistry, Biochemistry and Biotechnology for the Medicine, Via Saldini 50, Milano, Italy.

PMID: 18997937
DOI: 10.1039/b810447f

Abstract

N-Acetylneuraminic acid is transformed into its until now unavailable and rather unwieldy 1,7-lactone, via the manageable 2-benzyloxycarbonyl N-acetylneuraminic acid 1,7-lactone which generates the free lactone in quantitative yield by hydrogenolysis.

MeSH terms

Carbohydrate Conformation
Lactones / chemical synthesis*
Lactones / chemistry
Sialic Acids / chemical synthesis*
Sialic Acids / chemistry
Stereoisomerism

Substances

Lactones
N-acetylneuraminic acid 1,7-lactone
Sialic Acids