Chemoselective synthesis of sialic acid 1,7-lactones

  • J Org Chem. 2010 Aug 20;75(16):5542-8. doi: 10.1021/jo100732j.
Pietro Allevi  1 ,  Paola Rota ,  Raffaella Scaringi ,  Raffaele Colombo ,  Mario Anastasia
Affiliations
  • 1. Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università degli Studi di Milano, Via Saldini 50, I-20133 Milano, Italy.
PMID: 20704429 DOI: 10.1021/jo100732j
Abstract

The chemoselective synthesis of the 1,7-lactones of N-acetylneuraminic acid, N-glycolylneuraminic acid, and 3-deoxy-d-glycero-d-galacto-nononic acid is accomplished in two steps: a simple treatment of the corresponding free sialic acid with benzyloxycarbonyl chloride and a successive hydrogenolysis of the formed 2-benzyloxycarbonyl 1,7-lactone. The instability of the 1,7-lactones to protic Solvents has been also evidenced together with the rationalization of the mechanism of their formation under acylation conditions. The results permit to dispose of authentic 1,7-sialolactones to be used as reference standards and of a procedure useful for the preparation of their isotopologues to be used as inner standards in improved analytical procedures for the gas liquid chromatography-mass spectrometry (GLC-MS) analysis of 1,7-sialolactones in biological media.

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