87271-69-0Relevant articles and documents
Practical synthesis of potent sphingosine-1-phosphate lyase inhibitors THI and LX2931
Zhang, Haiming,Yan, Jie,Bednarz, Mark S.,Hernandez, Gonzalo,Lu, Yuelie,Courtney, Lawrence F.,Chen, Jason,Hu, Weifeng,Liu, Renmao,Yang, Xiaogen,Wu, Wenxue
, p. 4041 - 4046 (2013/06/26)
A practical and scalable synthesis of in vivo sphingosine-1-phosphate lyase inhibitor LX2931 (1) is described. The synthetic route features an improved Büchi cyclocondensation of 2-ethoxyacrylonitrile (3) with either 1-amino-1-deoxy-d-fructose acetate (4a) or d-(+)-glucosamine hydrochloride (4b) to produce 1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone (2, THI), followed by oximation of THI and acid-promoted oxime isomerization to give LX2931 (1).
