【结 构 式】 |
【分子编号】47272 【品名】3-hydroxy-2-[(1S,2R)-2-hydroxy-1-methylheptadecyl]-1-isoindolinone 【CA登记号】 |
【 分 子 式 】C26H43NO3 【 分 子 量 】417.63236 【元素组成】C 74.78% H 10.38% N 3.35% O 11.49% |
合成路线1
该中间体在本合成路线中的序号:(XIa)In a different procedure, dibenzyl malonate (VI) was alkylated with tetradecyl bromide (B) to afford (VII). This was then condensed with N-phthaloyl-L-alanyl chloride (VIII) in the presence of NaH, and the resulting keto diester (IX) was subjected to hydrogenolysis of the benzyl esters and further thermal decarboxylation to furnish ketone (X). Ketone reduction with simultaneous partial reduction of the phthaloyl group yielded (XI) and (XII) as a diastereomeric mixture. After chromatographic separation, the desired isomers were deprotected by reductive cleavage with NaBH4 to provide the corresponding amino alcohol.
【1】 Cuadros, R.; et al.; The marine compound spisulosine, an inhibitor of cell proliferation, promotes the disassembly of actin stress fibers. Cancer Letters 2000, 152, 1, 23. |
【2】 Garcia Gravalos, D.; Warwick, R.A.; Avila, J.; Rinehart, K.L.; Fregeau, N.L.; Faircloth, G.T. (University of Illinois); Spisulosine cpds. having antitumour activity. WO 9952521 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(B) | 47267 | 1-bromotetradecane | 112-71-0 | C14H29Br | 详情 | 详情 |
(XIa) | 47272 | 3-hydroxy-2-[(1S,2R)-2-hydroxy-1-methylheptadecyl]-1-isoindolinone | C26H43NO3 | 详情 | 详情 | |
(XIb) | 47273 | 3-hydroxy-2-[(1S,2S)-2-hydroxy-1-methylheptadecyl]-1-isoindolinone | C26H43NO3 | 详情 | 详情 | |
(XIIa) | 47274 | 2-(hydroxymethyl)-N-[(1S,2R)-2-hydroxy-1-methylheptadecyl]benzamide | C26H45NO3 | 详情 | 详情 | |
(XIIb) | 47275 | 2-(hydroxymethyl)-N-[(1S,2S)-2-hydroxy-1-methylheptadecyl]benzamide | C26H45NO3 | 详情 | 详情 | |
(VI) | 16013 | dibenzyl malonate | 15014-25-2 | C17H16O4 | 详情 | 详情 |
(VII) | 47268 | dibenzyl 2-tetradecylmalonate | C31H44O4 | 详情 | 详情 | |
(VIII) | 47269 | (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl chloride | C11H8ClNO3 | 详情 | 详情 | |
(IX) | 47270 | dibenzyl 2-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-2-tetradecylmalonate | C42H51NO7 | 详情 | 详情 | |
(X) | 47271 | 2-[(1S)-1-methyl-2-oxoheptadecyl]-1H-isoindole-1,3(2H)-dione | C26H39NO3 | 详情 | 详情 |