An efficient synthesis of l-idose and l-iduronic acid thioglycosides and their use for the synthesis of heparin oligosaccharides

• Published in: Carbohydrate research Vol. 343; no. 4; pp. 596 - 606
• Main Authors: Tatai, János, Osztrovszky, Györgyi, Kajtár-Peredy, Mária, Fügedi, Péter
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 17.03.2008; Elsevier
• Subjects: Biochemistry & Molecular Biology; Chemistry; Chemistry, Applied; Chemistry, Organic; Glycosylation; Heparin; Heparin - chemistry; Hexoses - chemistry; Iduronic Acid - chemistry; l-Iduronic acid; Life Sciences & Biomedicine; Molecular Structure; Oligosaccharide synthesis; Oligosaccharides - chemical synthesis; Oligosaccharides - chemistry; Physical Sciences; Science & Technology; Thioglycosides; Thioglycosides - chemical synthesis; Thioglycosides - chemistry; Oligosaccharide synthesis; Glycosylation; Heparin; l-Iduronic acid; Thioglycosides; ROUTE; thioglycosides; CONVERSION; BUILDING-BLOCKS; glycosylation; MOLECULAR DIVERSITY; heparin; PENTASACCHARIDE; L-iduronic acid; GLYCOSYL DONORS; SULFATE; MODULAR SYNTHESIS; PROTECTING GROUPS; DERIVATIVES; oligosaccharide synthesis
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2007.12.015

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.