71731-74-3Relevant articles and documents
Total Synthesis of the Potent and Broad-Spectrum Antibiotics Amycolamicin and Kibdelomycin
Chen, Chenglong,Chen, Jie,Li, Chao,Yang, Shaoqiang
supporting information, p. 21258 - 21263 (2021/12/17)
The complex and intriguing structures of the antibiotics amycolamicin and kibdelomycin are herein confirmed through total synthesis. Careful titration of the synthetic products reveals that kibdelomycin is the salt form of amycolamicin. This synthesis emp
An efficient and scalable synthesis of 2,4-di-N-acetyl-l-altrose (l-2,4-Alt-diNAc)
Niedzwiecka, Anna,Sequeira, Carita,Zhang, Ping,Ling, Chang-Chun
, p. 11583 - 11594 (2021/03/31)
Bacterial nonulosonic acids such as pseudaminic acids and others constitute a family of 9-carbon monosaccharides that contain a common 3-deoxy-2-ketoacid fragment but differ in their stereochemistries at 5 stereogenic centers between C-4 to C-8. Their unique structures make them attractive targets for use as antigens in vaccinations to combat drug-resistant bacterial infections and their challenging stereochemistries have attracted considerable attention from chemists. In this work we report the development of an improved synthesis for 2,4-di-N-acetyl-l-altrose (l-2,4-Alt-diNAc), which is a key hexose required for the chemical and chemoenzymatic synthesis of pseudaminic acids. Usingl-fucose as a starting material, our synthesis overcomes several pitfalls in previously reported syntheses.
Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger
Gu, Xiangying,Chen, Lin,Wang, Xin,Liu, Xiao,You, Qidong,Xi, Wenwei,Gao, Li,Chen, Guohua,Chen, Yue-Lei,Xiong, Bing,Shen, Jingkang
, p. 1100 - 1110 (2014/03/21)
A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-β-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
