Simultaneous stereoselective 4-amination with cyclic secondary amines and 2-O-deacetylation of peracetylated sialic acid derivatives |
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| Authors: | Deju Ye Jian Zhang Hualiang Jiang |
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| Affiliation: | a The Center for Drug Discovery and Design, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, PR China
b School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China |
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| Abstract: | Treatment of methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-β-l-glycero-d-galacto-2-nonulopyranosidonate (1) with cyclic secondary amines in pyridine at room temperature for 24 h afforded unusual products (2a-g). Related experiments were carried out to explain the formation of 4-amination and 2-O-deacetylation of peracetylated sialic acid derivatives (2a-g). This reaction may provide a new strategy for the preparation of Zanamivir analogues as neuraminidase inhibitors for anti-H5N1 subtype of avian influenza virus (AIV). |
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| Keywords: | Sialic acid derivatives Cyclic secondary amines Deacetylation Neu5Ac Neuraminidase inhibitors H5N1 |
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