A convenient synthesis of C-galactofuranosylic compounds (C-galactofuranosides).
Galactofuranose sugar units are essential for the production of the cell coat of many pathogenic microorganisms. This sugar is not found in mammals, and so compounds that may interfere with the biosynthetic processing of this sugar unit provide interesting targets for drug design. This paper describes the use of a cyanation reaction for the production of a one-carbon extension of a galactofuranosylic unit at C-1, giving 2,5-anhydro-3,4,6,7-tetra-O-benzoyl-D-glycero-L-manno-heptononitrile. A procedure for the efficient hydrolysis of the introduced nitrile group to produce the methyl ester is reported, along with procedures for the synthesis of both the corresponding alpha,beta-unsaturated, and 3-deoxy ester derivatives.
Owen
David J
DJ
Department of Medicinal Chemistry, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia
Thomson
Robin J
RJ
von Itzstein
Mark
M
D000995:Antitubercular Agents / Q000138:chemical synthesis; D015195:Drug Design; D005663:Furans / Q000138:chemical synthesis; D005697:Galactosides / Q000138:chemical synthesis*; D006027:Glycosides; D006868:Hydrolysis; D009005:Monosaccharides / Q000138:chemical synthesis*; D009570:Nitriles
D000995:Antitubercular Agents; C438934:C-glycoside; D005663:Furans; D005697:Galactosides; D006027:Glycosides; D009005:Monosaccharides; D009570:Nitriles