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【结 构 式】 
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【药物名称】DPIEL, NSC-710297, OMDPI 【化学名称】Phosphoric acid 2(R)-methoxy-3-octadecyloxypropyl 1(R),2(R),3(S),4(R),6(R)-tetrahydroxycyclohexyl diester 【CA登记号】253440-95-8, 213388-41-1 (racemate) 【 分 子 式 】C28H57O10P 【 分 子 量 】584.73429 |
【开发单位】Georgetown University (Originator) 【药理作用】Oncolytic Drugs, Inhibitors of Signal Transduction Pathways, Phosphatidylinositol Kinase Inhibitors, Protein Kinase B (PKB/Akt) Inhibitors |
合成路线1
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.
| 【1】 Qiao, L.; Nan, F.; Kunkel, M.; Gallegos, A.; Powis, G.; Kozikowski, A.P.; 3-Deoxy-D-myo-inositol 1-phosphate, 1-phosphonate, and ether lipid analogues as inhibitors of phosphatidylinositol-3-kinase signalling and cancer cell growth. J Med Chem 1998, 41, 18, 3303. |
| 【2】 Powis, G.; Qioa, L.; Kozikowski, A.P. (Georgetown University); Inhibitors of phosphatidyl myo-inositol cycle. WO 0000206 . |
| 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) | 40714 | (1R,2S,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexanol | C34H36O5 | 详情 | 详情 | |
| (II) | 40715 | C13H23N2OP | 详情 | 详情 | ||
| (III) | 40716 | C44H50NO6P | 详情 | 详情 | ||
| (IV) | 40717 | (2S)-2-methoxy-3-(octadecyloxy)-1-propanol | C22H46O3 | 详情 | 详情 | |
| (V) | 40718 | benzyl (2R)-2-methoxy-3-(octadecyloxy)propyl (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexyl phosphite | C63H87O9P | 详情 | 详情 | |
| (VI) | 40719 | benzyl (2R)-2-methoxy-3-(octadecyloxy)propyl (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexyl phosphate | C63H87O10P | 详情 | 详情 |