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 β-elimination, and a selective hydrolysis of the ester functions, without affecting the sensitive perfluorinated amide.
This journal is © The Royal Society of Chemistry 2012
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Acylation
-
Amines / chemistry*
-
Carbohydrates / chemical synthesis*
-
Carbohydrates / pharmacology
-
Cyclization
-
Enzyme Inhibitors / chemical synthesis*
-
Enzyme Inhibitors / pharmacology
-
Ether / chemistry*
-
Fluorine Compounds / chemical synthesis*
-
Fluorine Compounds / pharmacology
-
Molecular Structure
-
Neuraminic Acids / chemistry*
-
Neuraminidase / antagonists & inhibitors*
-
Structure-Activity Relationship
-
Vibrio cholerae / drug effects
-
Vibrio cholerae / enzymology
Substances
-
Amines
-
Carbohydrates
-
Enzyme Inhibitors
-
Fluorine Compounds
-
Neuraminic Acids
-
Ether
-
Neuraminidase