A facile synthesis of 2-deoxy-2,3-didehydroneuraminic acid derivatives.
The 2-thio- or 2-selenoglycosides of N-acetylneuraminic acid methyl ester were transformed by successive treatment with dimethyl(methylthio)sulfonium triflate (DMTST) and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) to give the corresponding methyl 2-deoxy-2,3-didehydroneuraminates in excellent yields. Their acids and their analogues are sialidase inhibitors of pharmaceutical interest.
Ikeda
K
K
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Konishi
K
K
Sano
K
K
Tanaka
K
K
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009439:Neuraminidase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D009439:Neuraminidase; D019158:N-Acetylneuraminic Acid