The Heyns Rearrangement Revisited: An Exceptionally Simple Two-Step Chemical Synthesis of D-Lactosamine from Lactulose.
The Heyns Rearrangement Revisited: An Exceptionally Simple Two-Step Chemical Synthesis of D-Lactosamine from Lactulose.
复制标题
重温海恩斯重排：从乳果糖中极其简单的两步化学合成 D-乳糖胺。
作者：
T. Wrodnigg;A. Stütz
在还原端含有d -氨基葡萄糖的双糖可以通过标题反应方便地以较高的产率由o -糖基化的d -果糖合成[式(a)]。研究了所有的双糖后，这种方法继续进行——大概是因为O-4上的糖基残基与其他极性基团之间明显的不稳定相互作用——比未取代的d-果糖有效得多，后者与氨反应生成d-氨基葡萄糖是由海恩斯和科赫在20世纪50年代描述的。
Disaccharides containing D-glucosamine at the reducing end can be conveniently synthesized in good yields from O-glycosylated D-fructoses by the title reaction [Eq. (a)]. With all the disaccharides investigated, the method proceeded-presumably because of the pronounced destabilizing interactions of the glycosyl residue at O-4 with the other polar groups-considerably more efficiently than with unsubstituted D-fructose, whose reaction with ammonia to give D-glucosamine was described by Heyns and Koch in the 1950s.