A method for obtaining equilibrium tautomeric mixtures of reducing sugars via glycosylamines using nonaqueous media.
Equilibrium tautomeric mixtures of several mono- and disaccharides are obtained in anhydrous form, without the use of water, by reacting the commercially available reducing sugars with ammonia gas in dry methanol, followed by the concentration of the resultant solution to dryness. Mutarotation and hydrolysis of the initially formed glycosylamine in the resultant medium account for the transformation. Equilibrium anomeric mixtures enriched in the beta-form of commercially available sugars such as alpha-D-glucose and alpha-lactose have not only vastly increased solubility, but are also synthetically valuable as these can be readily converted to the methyl/benzyl/trimethylsilyl ether and other derivatives for further transformations.
Allavudeen
Sikkander Sulthan
SS
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
Kuberan
Balagurunathan
B
Loganathan
Duraikkannu
D
D000588:Amines / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D000431:Ethanol / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D012995:Solubility
D000588:Amines; D004187:Disaccharides; D009005:Monosaccharides; D000431:Ethanol; D005947:Glucose