DPIEL, NSC-710297, OMDPI
Chemical Name: Phosphoric acid 2(R)-methoxy-3-octadecyloxypropyl 1(R),2(R),3(S),4(R),6(R)-tetrahydroxycyclohexyl diester
CAS No. 253440-95-8, 213388-41-1 (racemate)
项目整合开发状态: Preclinical
项目研究机构: Georgetown University (Originator)
合成路线:Phosphitylation of 1D-2,4,5,6-tetra-O-benzyl-3-deoxy-myo-inositol (I) with benzyl tetraisopropylphosphorodiamidite (II) in the presence of diisopropylammonium tetrazolide produced phosphoramidite (III).Subsequent displacement of the remaining diisopropylamino group of (III) by 1-O-octadecyl-2-O-methyl-sn-glycerol (IV) gave phosphite ester (V),which was further oxidized to phosphate (VI) using tert-butyl hydroperoxide.Finally,removal of the benzyl protecting groups of (VI) was achieved by catalytic hydrogenation over Pearlman's catalyst.
📌 参考资料/链接：
参考文献标题:Inhibitors of phosphatidyl myo-inositol cycle
文献作者:Powis,G.; Qioa,L.; Kozikowski,A.P.(Georgetown University)
参考来源:WO 0000206
📄 详细内容
合成路线:Phosphitylation of 1D-2,4,5,6-tetra-O-benzyl-3-deoxy-myo-inositol (I) with benzyl tetraisopropylphosphorodiamidite (II) in the presence of diisopropylammonium tetrazolide produced phosphoramidite (III).Subsequent displacement of the remaining diisopropylamino group of (III) by 1-O-octadecyl-2-O-methyl-sn-glycerol (IV) gave phosphite ester (V),which was further oxidized to phosphate (VI) using tert-butyl hydroperoxide.Finally,removal of the benzyl protecting groups of (VI) was achieved by catalytic hydrogenation over Pearlman's catalyst.
参考文献标题:3-Deoxy-D-myo-inositol 1-phosphate,1-phosphonate,and ether lipid analogues as inhibitors of phosphatidylinositol-3-kinase signalling and cancer cell growth
文献作者:Qiao,L.; Nan,F.; Kunkel,M.; Gallegos,A.; Powis,G.; Kozikowski,A.P.
参考来源:J Med Chem 1998,41(18),3303
产品链接: CAS No. 253440-95-8›› 产品链接: CAS No.213388-41-1››