One-pot-synthesis of alpha-linked deoxy sugar trisaccharides.
Various alpha-linked 2,6-dideoxy-ribo-trisaccharides, models for part of the antibiotic kijanimicin, were synthesised by the N-iodosuccinimide method employing different pathways. The efficiency of a sequential synthesis suffered from side reactions of the axial HO-3, which are typical of digitoxosides. These problems did not arise in a straightforward polymerisation, performed as a one-pot-procedure. It afforded the trisaccharide directly from the monosaccharide precursor in 30% yield. A combination of the oligomerisation pathway and the sequential synthesis led to trisaccharides with different protecting group patterns. In these reactions different glycal and alcohol components were used and allowed to define the optimal partners in a sequential synthesis: the two components should ideally be of comparable reactivity.
Köpper
S
S
Institut für Organische Chemie, Universität Hamburg, Germany.
Thiem
J
J
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009904:Optical Rotation; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D014312:Trisaccharides