D-t-EtDO-P4
N-[1-(2,3-二氢-1,4-苯并二氧杂环己-6-基)-1-羟基-3-(1-吡咯烷基)-2-丙基]十六烷酰胺Chemical Name: N-[(1R,2R)-2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-hydroxy-1-(1-pyrrolidinylmethyl)ethyl]hexadecanamide
CAS No. 245329-78-6
项目整合开发状态: Preclinical
项目研究机构: National Institutes of Health (Originator), University of Michigan (Originator)
合成路线:The condensation of 2,3-dihydrobenzodioxin-6-carbaldehyde (I) with 5(S)-phenylmorpholin-2-one (I) in refluxing toluene gives the adduct (III),which is treated first with pyrrolidine (IV) in chloroform and then with HCl in refluxing methanol to yield the pyrrolidide (V).The reduction of (V) with LiAlH4 in THF affords compound (VI),which is treated with H2 over Pd/C in THF/methanol/water to provide the aminoalcohol (VII).Finally,the amino group of (VII) is acylated by means of palmitoyl chloride (VIII) and DIEA in dichloromethane to furnish the target palmitoylamide.
📌 参考资料/链接：
参考文献标题:Synthesis of UDP-glucose: N-Acylsphingosine glucosyltransferase inhibitors
文献作者:Hirth,B.H.; Siegel,C.(Genzyme Corp.)
参考来源:US 2003050299; WO 0308399
📄 详细内容
合成路线:Methenamine is added to a solution of bromide (I) in CHCl3 and after treatment with concentrated HCl,amine (II) is obtained.NaOAc and palmitoyl chloride (III) are added to a solution of (II) in THF to yield derivative (IV) which is finally converted to (V) by treatment with paraformaldehyde and pyrrolidine in ethanol,followed by treatment with concentrated HCl,reduction with NaBH4 and final hydrolysis with diluted HCl.
参考文献标题:Improved inhibitors of glucosylceramide synthase
文献作者:Lee,L.; Abe,A.; Shayman,J.A.
参考来源:J Biol Chem 1999,274(21),14662
产品链接: CAS No. 245329-78-6››