BrHPP sodium salt
Chemical Name: Diphosphoric acid 4-bromo-3-hydroxy-3-methylbutyl ester trisodium salt
项目整合开发状态: Preclinical
项目研究机构: INSERM (Originator)
合成路线:The reaction of 3-methyl-3-buten-1-ol (I) with tosyl chloride and DMAP in dichloromethane gives the corresponding tosylate (II),which is condensed with tetrakis tetrabutylammonium pyrophosphate (III) in acetonitrile and purified through Dowex 50-WXB-200 (NH4+),yielding the corresponding ester (IV) as an ammonium salt.Finally,this compound is brominated with Br2 in water and purified through Dowex 50-WXB-200 (Na+) to afford the target compound.The intermediate tetrakis tetrabutylammonium pyrophosphate (III) has been obtained as follows: Disodium pyrophosphate (V) is deionized by means of Dowex 50-WXB-200 (H+) to give pyrophosphoric acid (VI),which is then neutralized with tetrabutylammonium hydroxide in water affording the target pyrophosphate (III).
📌 参考资料/链接：
参考文献标题:Phosphohalohydrins,method for making same and uses
文献作者:Peyrat,M.-A.; Bonneville,M.; Fournie,J.-J.; Belmant,C.(INSERM (Institut National de la Sante et de la Recherche Medicale))
参考来源:FR 2782721; WO 0012516
📄 详细内容
合成路线:The reaction of 3-methyl-3-buten-1-ol (I) with tosyl chloride and DMAP in dichloromethane gives the corresponding tosylate (II),which is condensed with tetrakis tetrabutylammonium pyrophosphate (III) in acetonitrile and purified through Dowex 50-WXB-200 (NH4+),yielding the corresponding ester (IV) as an ammonium salt.Finally,this compound is brominated with Br2 in water and purified through Dowex 50-WXB-200 (Na+) to afford the target compound.The intermediate tetrakis tetrabutylammonium pyrophosphate (III) has been obtained as follows: Disodium pyrophosphate (V) is deionized by means of Dowex 50-WXB-200 (H+) to give pyrophosphoric acid (VI),which is then neutralized with tetrabutylammonium hydroxide in water affording the target pyrophosphate (III).
参考文献标题:Chemical synthesis and biological activity of bromohydrin pyrophosphate,a potent stimulator of human gammadelta T cells
文献作者:Espinosa,E.; Belmant,C.; Pont,F.; Luciani,B.; Poupot,R.; Romagne,F.; Brailly,H.; Bonneville,M.; Fournie,J.J.
参考来源:J Biol Chem 2001,276(21),18337