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【结 构 式】 
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【药物名称】Sitostanol ascorbyl phosphate 【化学名称】Phosphoric acid [(3beta,5alpha,24R)-stigmastan-3-yl] L-ascorbic acid-2-O-yl diester disodium salt 【CA登记号】315179-26-1 (monosodium salt) 【 分 子 式 】C35H57Na2O9P 【 分 子 量 】698.79254 |
【开发单位】Forbes Medi-Tech (Originator) 【药理作用】Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Lipid Lowering Agents |
合成路线1
Reaction of sitostanol (I) with phosphorus oxychloride and pyridine affords the dichlorophosphoryl compound (II). Ascorbic acid (III) is protected as the 5,6-isopropylidene ketal (IV) upon treatment with acetone and fuming sulfuric acid. Condensation of (IV) with acid chloride (II) provides the phosphoryl monochloride (V), which is hydrolyzed under acidic conditions to yield the phosphate diester (VI). Finally, compound (VI) is converted to the target disodium salt by using an ethanolic solution of NaOMe. (1,2)
| 【1】 Chen, H.; Milanova, R.K.; Kutney, J.P.; Hou, D.; Ding, Y. (Forbes Medi-Tech Inc.); Conjugates of phytosterol or phytostanol with ascorbic acid and use thereof in treating or preventing cardiovascular disease. JP 2003522124; WO 0100653 . |
| 【2】 Novak, E.; Milanova, R.K.; Kutney, J.P.; Pritchard, H.P.; Lukic, T. (Forbes Medi-Tech Inc.); Novel structures comprising phytosterol and/or phytostanol and ascorbic acid and use thereof as weight regulating agents. WO 0234241 . |
| 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) | 64797 | (3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | C29H52O | 详情 | 详情 | |
| (II) | 64798 | C29H51Cl2O2P | 详情 | 详情 | ||
| (III) | 29820 | (5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2(5H)-furanone | 50-81-7 | C6H8O6 | 详情 | 详情 |
| (IV) | 64794 | (5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2(5H)-furanone | C9H12O6 | 详情 | 详情 | |
| (V) | 64799 | C38H62ClO8P | 详情 | 详情 | ||
| (VI) | 64800 | (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-2-oxo-2,5-dihydro-3-furanyl (3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethylhexyl]-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl hydrogen phosphate | C35H59O9P | 详情 | 详情 |