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【结 构 式】 
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【分子编号】39594 【品名】3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(3-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaenyl]-2,4,4-trimethyl-2-cyclohexen-1-ol 【CA登记号】 |
【 分 子 式 】C40H56O2 【 分 子 量 】568.88344 【元素组成】C 84.45% H 9.92% O 5.62% |
合成路线1
该中间体在本合成路线中的序号：(XIX)The reaction of vitamin A aldehyde (retinene) (XV) with NBS and acetic acid - acetic anhydride in CHCl3 gives 3-acetoxyretinene (XVI), which is reduced with NaBH4 in methanol to yield 3-acetoxyretinol (XVII). The reaction of (XVII) with triphenylphosphine and HCl in methanol affords 3-acetoxyretinyltriphenylphosphonium chloride (XVIII), which is condensed through a Wittig reaction with aldehyde (XVI) by means of sodium methoxide in isopropanol giving trans-isozeaxanthin (XIX). Finally, this compound is oxidized with aluminum isopropoxide in refluxing benzene - acetone.
| 【1】 Surmatis, J.D.; et al.; Synthesis of oxygenated carotenoids. Helv Chim Acta 1970, 53, 5, 974-990. |
| 【2】 Surmatis, J.D.; US 3311656 . |
| 【3】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Canthazanthin. Drugs Fut 1979, 4, 7, 477. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 39590 | (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal | C20H28O | 详情 | 详情 | |
| (XVI) | 39591 | 3-[(1E,3E,5E,7E)-3,7-dimethyl-9-oxo-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate | C22H30O3 | 详情 | 详情 | |
| (XVII) | 39592 | 3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethyl-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate | C22H32O3 | 详情 | 详情 | |
| (XVIII) | 39593 | [(2E,4E,6E,8E)-9-[3-(acetoxy)-2,6,6-trimethyl-1-cyclohexen-1-yl]-3,7-dimethyl-2,4,6,8-nonatetraenyl](triphenyl)phosphonium chloride | C40H46ClO2P | 详情 | 详情 | |
| (XIX) | 39594 | 3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(3-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaenyl]-2,4,4-trimethyl-2-cyclohexen-1-ol | C40H56O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIX)Finally, compound (XXIII) by reaction with NBS and acetic acid in CHCl3, followed by a treatment with KOH in methanol, is converted into the previously obtained diol (XIX).
| 【1】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Canthazanthin. Drugs Fut 1979, 4, 7, 477. |
| 【2】 Surmatis, J.D.; et al.; Synthesis of oxygenated carotenoids. Helv Chim Acta 1970, 53, 5, 974-990. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIX) | 39594 | 3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(3-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaenyl]-2,4,4-trimethyl-2-cyclohexen-1-ol | C40H56O2 | 详情 | 详情 | |
| (XXIII) | 39598 | 1,5,5-trimethyl-6-[(Z,2E,4E,6E,8E,10E,12E,14E,16E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2,4,6,8,10,12,14,16-octadecaoctaenylidene]-1-cyclohexene | C40H54 | 详情 | 详情 |