【结 构 式】 |
【分子编号】28801 【品名】1-(benzyloxy)-1,2-ethanediol 【CA登记号】 |
【 分 子 式 】C9H12O3 【 分 子 量 】168.19248 【元素组成】C 64.27% H 7.19% O 28.54% |
合成路线1
该中间体在本合成路线中的序号:(XII)Two different routes have been described for the preparation of Et-18-OCH3: 1) The methylation of 1,3-benzylideneglycerol (I) with methyl iodide and KOH gives 1,3-benzytidene-2-O-methylglycerol (II), which is hydrolyzed with HCl to 2-O-methylglycerol (III). The condensation of (III) with octadecyl bromide (IV) and KOH in DMSO/THF yields 1-O-octadecyl-2-O-methyl-(rac)-glycerol (V), which by reaction with phosphorodichloric acid 2-bromoethyl ester (VI) and pyridine is converted to 3-octadecyloxy-2-methoxypropyl bromoethyl phosphate (VII). Finally, this compound is converted to Et-18-OCH3 with trimethylamine (VIII) in toluene and treated with silver carbonate to remove traces of bromide. 2) The reaction of 1,2-isopropylidene-sn-glycerol (IX) with benzyl bromide (X) and NaNH2 in benzene gives 1,2-isopropylidene-3-O-benzyl-sn-glycerol (XI), which is hydrolyzed with acetic acid to 3-O-benzyl-sn-glycerol (XII). The etherification of (XII) with (IV) as before or with NaNH2 gives 1-O-octadecyl-3-O-benzyl-sn-glycerol (XIII), which is methylated with methyl iodide and NaNH2 in dioxane to give 1-O-octadecyl-2-O-methyl-3-O-benzyl-sn-glycerol (XIV). Finally, this compound is debenzytaled by hydrogenolysis with H2 over Pd/C in petroleum ether to form (V), an intermediate previously described above.
【1】 Tsutsumi, H.; Kamata, T.; Nakajima, K.; Katagi, M.; Tsuchihashi, H.; Nishioka, H.; Nishikawa, M.; Miki, A.; Tatsuno, M.; Chem Phys Lipids 1982, 30, 9, 389-392. |
【2】 Fast, L.D.; et al.; Chem Pharm Bull 1982, 30, 9, 3260-3270. |
【3】 Castaner, R.M.; Castaner, J.; Serradell, M.N.; ET-18-OCH3. Drugs Fut 1987, 12, 4, 341. |
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) | 28795 | 2-phenyl-1,3-dioxan-5-ol | 1708-40-3 | C10H12O3 | 详情 | 详情 |
(II) | 28796 | 5-methoxy-2-phenyl-1,3-dioxane | C11H14O3 | 详情 | 详情 | |
(III) | 13579 | 2-Methoxy-1,3-propanediol | C4H10O3 | 详情 | 详情 | |
(IV) | 28797 | 1-bromooctadecane | 112-89-0 | C18H37Br | 详情 | 详情 |
(V) | 28798 | 2-methoxy-3-(octadecyloxy)-1-propanol | C22H46O3 | 详情 | 详情 | |
(VI) | 13033 | Dichlorophosphoric acid 2-bromoethyl ester | C2H4BrCl2O2P | 详情 | 详情 | |
(VII) | 28799 | 2-bromoethyl 2-methoxy-3-(octadecyloxy)propyl hydrogen phosphate | C24H50BrO6P | 详情 | 详情 | |
(IX) | 16476 | 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane; (2,2-dimethyl-1,3-dioxolan-4-yl)methanol; 2,3-o-Isopropylideneglycerol | 100-79-8 | C6H12O3 | 详情 | 详情 |
(X) | 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 |
(XI) | 28800 | benzyl 2,2-dimethyl-1,3-dioxolan-4-yl ether | C12H16O3 | 详情 | 详情 | |
(XII) | 28801 | 1-(benzyloxy)-1,2-ethanediol | C9H12O3 | 详情 | 详情 | |
(XIII) | 28802 | 1-(benzyloxy)-2-(octadecyloxy)-1-ethanol | C27H48O3 | 详情 | 详情 | |
(XIV) | 28803 | 1-[[1-methoxy-2-(octadecyloxy)ethoxy]methyl]benzene | C28H50O3 | 详情 | 详情 |