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【结 构 式】 
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【分子编号】52822 【品名】(2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1~2,6~.0~7,28~.0~8,13~.0~15,19~.0~20,27~.0~21,26~]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one 【CA登记号】 |
【 分 子 式 】C28H26N4O3 【 分 子 量 】466.5396 【元素组成】C 72.09% H 5.62% N 12.01% O 10.29% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of staurosporine (I) with benzyl chloroformate (II) by means of NaHCO3 in acetone gives the N-protected compound (II), which is oxidized with lead tetraacetate in HOAc to yield the hydroxy compound (III). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C in DMF to obtain the target hydroxy staurosporine.
| 【1】 Murakata, C.; Sato, A.; Kasai, M.; Morimoto, M.; Akinaga, S. (Kyowa Hakko Kogyo Co., Ltd.); Staurosporin derivatives. EP 0383919; JP 2766360B2; WO 8907105 . |
| 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) | 52822 | (2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1~2,6~.0~7,28~.0~8,13~.0~15,19~.0~20,27~.0~21,26~]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one | C28H26N4O3 | 详情 | 详情 | |
| (II) | 56662 | benzyl (2S,4R,6R)-3-methoxy-2-methyl-16-oxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1~2,6~.0~7,28~.0~8,13~.0~15,19~.0~20,27~.0~21,26~]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-4-yl(methyl)carbamate | C36H32N4O5 | 详情 | 详情 | |
| (III) | 56663 | benzyl (2S,4R,6R)-18-hydroxy-3-methoxy-2-methyl-16-oxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1~2,6~.0~7,28~.0~8,13~.0~15,19~.0~20,27~.0~21,26~]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-4-yl(methyl)carbamate | C36H32N4O6 | 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 title benzamide was prepared by acylation of the alkaloid staurosporine (I) with benzoyl chloride (II) in the presence of diisopropylethylamine in chloroform.
| 【1】 Caravatti, G.; et al.; Inhibitory activity and selectivity of staurosporine derivatives towards protein kinase C. Bioorg Med Chem Lett 1994, 4, 3, 399. |
| 【2】 Caravatti, G.; Fredenhagen, A. (Novartis AG); Staurosporine derivs. substd. for the nitrogen atom of the methylamino group. EP 0296110; JP 1989034989; US 5093330 . |