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【结 构 式】 
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【分子编号】40038 【品名】(2S)-2-amino-N-[[(1R,2S,10R,12R,13S)-12-cyano-19-hydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8-dioxo-11,21-diazapentacyclo[11.7.1.0(2,11).0(4,9).0(15,20)]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl]propanamide 【CA登记号】 |
【 分 子 式 】C29H35N5O6 【 分 子 量 】549.627 【元素组成】C 63.37% H 6.42% N 12.74% O 17.47% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of cyanosafracin B (I) with Boc2O in ethanol gives the amino protected compound (II), which is treated with Mom-Br, DIEA and DMAP in acetonitrile yielding the O-protected compound (III). The demethylation of (III) with NaOH in methanol affords the hydroxyquinone (IV), which is reduced with H2 over Pd/C and cyclized with bromochloromethane and Cs2CO3 in hot DMF providing the methylenedioxy compound (V). The reaction of (V) with acetyl chloride and pyridine in dichloromethane gives the acetate (VI), which is treated with TFA, phenyl isothiocyanate and HCl yielding the primary amine (VII). Finally, this compound is treated with phthalic anhydride (VIII) and CDI in dichloromethane to afford the target phthalimide (phthalascidin Pt-650).
| 【1】 Cuevas, C.; Martin, M.J.; Perez, M.; et al.; Synthesis of ecteinascidin ET-743 and phathalascidin Pt-650 from cyanosafracin B. Org Lett 2000, 2, 16, 2545. |
| 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) | 40038 | (2S)-2-amino-N-[[(1R,2S,10R,12R,13S)-12-cyano-19-hydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8-dioxo-11,21-diazapentacyclo[11.7.1.0(2,11).0(4,9).0(15,20)]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl]propanamide | C29H35N5O6 | 详情 | 详情 | |
| (II) | 40039 | tert-butyl (1S)-2-([[(1R,2S,10R,12R,13S)-12-cyano-19-hydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8-dioxo-11,21-diazapentacyclo[11.7.1.0(2,11).0(4,9).0(15,20)]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl]amino)-1-methyl-2-oxoethylcarbamate | C34H43N5O8 | 详情 | 详情 | |
| (III) | 40040 | tert-butyl (1S)-2-([[(1R,2S,10R,12R,13S)-12-cyano-7,18-dimethoxy-19-(methoxymethoxy)-6,17,21-trimethyl-5,8-dioxo-11,21-diazapentacyclo[11.7.1.0(2,11).0(4,9).0(15,20)]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl]amino)-1-methyl-2-oxoethylcarbamate | C36H47N5O9 | 详情 | 详情 | |
| (IV) | 40041 | tert-butyl (1S)-2-([[(1R,2S,10R,12R,13S)-12-cyano-7-hydroxy-18-methoxy-19-(methoxymethoxy)-6,17,21-trimethyl-5,8-dioxo-11,21-diazapentacyclo[11.7.1.0(2,11).0(4,9).0(15,20)]henicosa-4(9),6,15,17,19-pentaen-10-yl]methyl]amino)-1-methyl-2-oxoethylcarbamate | C35H45N5O9 | 详情 | 详情 | |
| (V) | 40042 | C36H47N5O9 | 详情 | 详情 | ||
| (VI) | 40043 | C38H49N5O10 | 详情 | 详情 | ||
| (VII) | 40044 | (1R,2S,13R,15R,16S)-13-(aminomethyl)-15-cyano-22-hydroxy-21-methoxy-6,20,24-trimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaen-5-yl acetate | C28H32N4O6 | 详情 | 详情 | |
| (VIII) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |