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【结 构 式】

【分子编号】47274

【品名】2-(hydroxymethyl)-N-[(1S,2R)-2-hydroxy-1-methylheptadecyl]benzamide

【CA登记号】

【 分 子 式 】C26H45NO3

【 分 子 量 】419.64824

【元素组成】C 74.42% H 10.81% N 3.34% O 11.44%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XIIa)

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
Extended Information