Trityl-cyanoethylidene condensation of azidosugar derivatives as a route to hexosaminoglycans. Synthesis of the O-antigenic polysaccharide of Pseudomonas aeruginosa X (Meitert)
Yu. E. Tsvetkov, L. V. Backinowsky, N. K. Kochetkov
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Derivatives of azidosugars were shown to be stable under conditions of trityl-cyanoet-hylidene condensation. Tritylated 1,2-O-(1-cyano)ethylidene derivative of 2-azido-2-deoxy-β-D-mannopyranosyl-(1→4)-L-rhamnopyranose was used as a starting material for the synthesis of [→3)-β-D-ManNAc-(1→4)-α-L-Rha-(1→]n, the O-specific polysaccharide of Pseudomonas aeruginosa X (Meitert).
Russian Journal of Bioorganic Chemistry 1991, 17 (11):1534-1549