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【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information