An efficient synthesis of L-idose and L-iduronic acid thioglycosides and their use for the synthesis of heparin oligosaccharides.
Efficient preparations of thioglycoside derivatives of L-idose and L-iduronic acid are described. The method avoids the tedious chromatographic separations of furanose and pyranose anomeric mixtures, and affords the thioglycosides in a stereoselective manner. The L-idose and L-iduronic acid thioglycosides having combinations of different protecting groups proved to be efficient glycosyl donors in the synthesis of heparin disaccharides.
Tatai
János
J
Department of Carbohydrate Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary.
Osztrovszky
Györgyi
G
Kajtár-Peredy
Mária
M
Fügedi
Péter
P
D006493:Heparin / Q000737:chemistry*; D006601:Hexoses / Q000737:chemistry*; D007067:Iduronic Acid / Q000737:chemistry*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
D006601:Hexoses; D009844:Oligosaccharides; D013865:Thioglycosides; C010997:idose; D007067:Iduronic Acid; D006493:Heparin