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【结 构 式】 
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【分子编号】23090 【品名】1-hexadecanol 【CA登记号】36653-82-4 |
【 分 子 式 】C16H34O 【 分 子 量 】242.44536 【元素组成】C 79.27% H 14.14% O 6.6% |
合成路线1
该中间体在本合成路线中的序号：(I)In scheme 14476001a hexadecanol is reacted with phosphoroxy chloride in the presence of triethylamine in tetrahydrofuran with subsequent condensation with ethanolamine in dioxane/triethylamine. Hydrolysis with aqueous hydrochloric acid and methylation with dimethyl sulfate in the presence of potassium carbonate yields hexadecyl phosphocholine.
| 【1】 Schumacher, W.; Unger, C.; Berger, M.R.; Hilgard, P.; Eibl, H.J.; Schmahl, D.; Stekar, J.; Engel, J.; Nagel, G.; Hexadecylphocholine. Drugs Fut 1988, 13, 11, 948. |
| 【2】 Kin, D.J.; Unger, C.; Berger, M.R.; Fleer, E.A.M.; Nagel, G.A.; Eibl, H.; Hexadecylphosphocholine, a new antineoplastic agent: cytotoxic properties in leukaemic cells. J Cancer Res Clin Oncol 1986, 111, 24. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 | |
| (I) | 23090 | 1-hexadecanol | 36653-82-4 | C16H34O | 详情 | 详情 |
| (II) | 23091 | Dichlorophosphoric acid hexadecyl ester | C16H33Cl2O2P | 详情 | 详情 | |
| (III) | 23092 | 2-(hexadecyloxy)-1,3,2lambda(5)-oxazaphospholidin-2-one | C18H38NO3P | 详情 | 详情 | |
| (IV) | 23093 | Phosphoric acid 2-aminoethyl hexadecyl diester inner salt | C19H40O4P | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The reaction of hexadecanol (I) with the cyclic chlorophosphate ester (II) and TEA in tert-butyl methyl ether gives the cyclic hexadecyl phosphate (III), which is condensed with TEA in hot acetonitrile to afford the target phosphorylcholine ester.
| 【1】 Bittman, R.; Lohmeyer, M.; Antitumor ether lipids and alkylphosphocholines. Drugs Fut 1994, 19, 11, 1021. |
| 【2】 Nossner, G.; Stekar, J.; Hilgard, P.; et al.; D-21266, ein neues Alkylphospholipid mit hoder antineoplasticher Wirkung und verbessertem therapeutischen Index. ASTA Medica 1993. |
合成路线3
该中间体在本合成路线中的序号：(I)The reaction of hexadecanol (I) with the cyclic chlorophosphate ester (II) and DIEA in dichloromethane gives the cyclic hexadecyl phosphate (III), which is brominated with Br2 in the same solvent to yield the mixed 2-bromoethyl hexadecyl bromophosphate ester (IV). Finally this compound is condensed with trimethylamine in acetonitrile/isopropanol/chloroform to furnish the target phosphorylcholine ester.
| 【1】 Bittman, R.; Lohmeyer, M.; Antitumor ether lipids and alkylphosphocholines. Drugs Fut 1994, 19, 11, 1021. |
| 【2】 Reddy, K.C.; Byun, H.S.; Bittman, R.; Antitumor ether lipids: An improved synthesis of ilmofosine and an enantioselective synthesis of an ilmofosine analog. Tetrahedron Lett 1994, 35, 17, 2679. |