Synthesis of 2-deoxy-2-(4-nitroimidazol-1-yl)-D-alditols.
Small molecules possessing defined configuration at centres of chirality provide a valuable chiral pool. Among different strategies applied for modification of chiral compounds, the most common is to begin with a single stereoisomer and use a synthesis that does not affect the chiral centres. The ANRORC type reaction has been applied for conversion of unprotected 2-amino-2-deoxy-D-hexopyranoses into 2-deoxy-2-(4-nitroimidazol-1-yl)-D-hexopyranoses in a reaction of some 2-aminosugars with 1,4-dinitroimidazoles. The reaction occurs with retention of configuration at C-2 of sugar ring. The products of the reaction were obtained as anomeric mixtures and separated into anomers after acetylation followed by column chromatography. 2-Deoxy-2-(4-nitroimidazol-1-yl)-D-hexopyranoses treated with sodium borohydride in methanolic solution gave the corresponding 2-deoxy-2-(4-nitroimidazol-1-yl)-D-hexitols, characterised as per-O-acetylated derivatives.
Gondela
Andrzej
A
Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland.
Walczak
Krzysztof
K
D000606:Amino Sugars / Q000737:chemistry; D009593:Nitroimidazoles / Q000737:chemistry*; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis*
D000606:Amino Sugars; D009593:Nitroimidazoles; D013402:Sugar Alcohols