【结 构 式】 |
【分子编号】47476 【品名】tetra(N,N,N-tributyl-1-butanaminium) phosphonatomethylphosphonate 【CA登记号】 |
【 分 子 式 】C65H146N4O6P2 【 分 子 量 】1141.845124 【元素组成】C 68.37% H 12.89% N 4.91% O 8.41% P 5.43% |
合成路线1
该中间体在本合成路线中的序号:(III)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).
【1】 Espinosa, E.; et al.; Chemical synthesis and biological activity of bromohydrin pyrophosphate, a potent stimulator of human gammadelta T cells. J Biol Chem 2001, 276, 21, 18337. |
【2】 Peyrat, M.-A.; Bonneville, M.; Fournie, J.-J.; Belmant, C. (INSERM (Institut National de la Sante et de la Recherche Medicale)); Phosphohalohydrins, method for making same and uses. FR 2782721; WO 0012516 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 47474 | 3-methyl-3-buten-1-ol | 763-32-6 | C5H10O | 详情 | 详情 |
(II) | 47475 | 3-methyl-3-butenyl 4-methylbenzenesulfonate | C12H16O3S | 详情 | 详情 | |
(III) | 47476 | tetra(N,N,N-tributyl-1-butanaminium) phosphonatomethylphosphonate | C65H146N4O6P2 | 详情 | 详情 | |
(IV) | 47477 | triammonium [[(3-methyl-3-butenyl)oxy]phosphinato]methylphosphonate | C6H23N3O6P2 | 详情 | 详情 | |
(V) | 47478 | disodium (hydroxyphosphinato)methylphosphonate | CH4Na2O6P2 | 详情 | 详情 | |
(VI) | 47479 | phosphonomethylphosphonic acid | 1984-15-2 | CH6O6P2 | 详情 | 详情 |