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Org Biomol Chem ; 10(14): 2885-94, 2012 Apr 14.
Article in English | MEDLINE | ID: mdl-22395901

ABSTRACT

A simple protocol for the synthesis of N-perfluoroacylated and N-acylated glycals of neuraminic acid, with a secondary cyclic amine (morpholine or piperidine) at the 4α position, has been set-up, starting from peracetylated N-acetylneuraminic acid methyl ester that undergoes, sequentially to its direct N-transacylation followed by a C-4 amination, a ß-elimination, and a selective hydrolysis of the ester functions, without affecting the sensitive perfluorinated amide.


Subject(s)
Amines/chemistry , Carbohydrates/chemical synthesis , Enzyme Inhibitors/chemical synthesis , Ether/chemistry , Fluorine Compounds/chemical synthesis , Neuraminic Acids/chemistry , Neuraminidase/antagonists & inhibitors , Acylation , Carbohydrates/pharmacology , Cyclization , Enzyme Inhibitors/pharmacology , Fluorine Compounds/pharmacology , Molecular Structure , Structure-Activity Relationship , Vibrio cholerae/drug effects , Vibrio cholerae/enzymology
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