Allavudeen Sikkander Sulthan, Kuberan Balagurunathan, Loganathan Duraikkannu
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
Carbohydr Res. 2002 May 13;337(10):965-8. doi: 10.1016/s0008-6215(02)00075-7.
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.
通过将市售还原糖与氨气在无水甲醇中反应，然后将所得溶液浓缩至干，无需用水即可获得几种单糖和二糖的无水形式的平衡互变异构混合物。所得介质中最初形成的糖基胺的变旋和水解导致了这种转化。富含市售糖（如α-D-葡萄糖和α-乳糖）β-型的平衡异头物混合物不仅溶解度大大提高，而且在合成上也很有价值，因为它们可以很容易地转化为甲基/苄基/三甲基硅烷基醚和其他衍生物以进行进一步转化。
