有机化学 ›› 2014, Vol. 34 ›› Issue (5): 926-932.DOI: 10.6023/cjoc201312028 上一篇    下一篇

研究论文

异乳糖的合成研究

姜锐, 梁晓梅, 金淑慧, 张建军, 王道全   

  1. 中国农业大学理学院应化系 北京 100193
  • 收稿日期:2013-12-22 修回日期:2014-01-13 发布日期:2014-02-10
  • 通讯作者: 张建军 E-mail:zhangjianjun@cau.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21172257)和十二五科技支撑计划(Nos. 2012BAK25B03-01,2011AA10A206)资助项目.

Efficient Synthesis of Allolactose

Jiang Rui, Liang Xiaomei, Jin Shuhui, Zhang Jianjun, Wang Daoquan   

  1. Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2013-12-22 Revised:2014-01-13 Published:2014-02-10
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21172257) and the National S&T Pillar Program of China (Nos. 2012BAK25B03-01, 2011AA10A206).

异乳糖是一种还原性双糖,在细菌的代谢过程中有着非常重要的生物学作用. 以D-葡萄糖、D-半乳糖为起始原料,探索了异乳糖的多羟基区域选择性偶联与非选择性偶联两条合成路线,其中非选择性偶联路线经五锅反应,总收率高达44%,中间体及目标产物易于分离纯化,适宜于异乳糖的大量制备. 中间体及最终产物的结构均通过NMR,HRMS进行表征.

关键词: 异乳糖, D-葡萄糖, D-半乳糖, 合成

Allolactose (β-D-galactopyranosyl-(1→6)-α,β-D-glucopyranose) is a reducing disaccharide playing important biological role in bacterial metabolism. Two synthetic methods of allolactose including regioselective glycosylation and stepwise synthesis were investigated using D-glucose and D-galactose as the starting materials. The later approach involved a five-spot strategy, 44% overall yields and all the intermediates were easily to be purified, making the route suitable for large scale preparation of the target compound. All the compounds were characterized by NMR and HRMS spectra.

Key words: allolactose, D-glucose, D-galactose, synthesis