Two simple and rapid procedures affording 4 beta-acylamido- and 4 beta-acetoxyneuraminic acid glycals acylated or perfluoroacylated at the 5-amino group are reported. The first protocol avoids the formation of oxazolines to synthesize the 4 beta-acetamido glycals through the Ritter reaction. The second passes through the oxazoline derivative to prepare 4 beta-acetoxyneuraminic acid glycals. Both protocols start from peracetylated methyl neuraminate, acylated at the amino group with a normal, a glycolyl, or a perfluoroacyl group, or with the corresponding peracetylated glycal methyl esters (of the DANA or FANA series).
Simple and Rapid Procedures for the Synthesis of 5-Acylated 4 beta-Acylamido- and 4 beta-Acetoxyneuraminic Acid Glycals / I.S. Agnolin, P. Rota, P. Allevi, A. Gregorio, M. Anastasia. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2012:33(2012 Nov), pp. 6537-6547. [10.1002/ejoc.201201001]
Simple and Rapid Procedures for the Synthesis of 5-Acylated 4 beta-Acylamido- and 4 beta-Acetoxyneuraminic Acid Glycals
I.S. AgnolinPrimo
;P. RotaSecondo
;P. Allevi;A. GregorioPenultimo
;M. AnastasiaUltimo
2012
Abstract
Two simple and rapid procedures affording 4 beta-acylamido- and 4 beta-acetoxyneuraminic acid glycals acylated or perfluoroacylated at the 5-amino group are reported. The first protocol avoids the formation of oxazolines to synthesize the 4 beta-acetamido glycals through the Ritter reaction. The second passes through the oxazoline derivative to prepare 4 beta-acetoxyneuraminic acid glycals. Both protocols start from peracetylated methyl neuraminate, acylated at the amino group with a normal, a glycolyl, or a perfluoroacyl group, or with the corresponding peracetylated glycal methyl esters (of the DANA or FANA series).Pubblicazioni consigliate
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