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【结 构 式】 
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【分子编号】22889 【品名】7-[[amino(imino)methyl]amino]-N-[2-([4-[(3-aminopropyl)amino]butyl]amino)-2-oxo-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]heptanamide 【CA登记号】 |
【 分 子 式 】C22H45N7O4 【 分 子 量 】471.64408 【元素组成】C 56.03% H 9.62% N 20.79% O 13.57% |
合成路线1
该中间体在本合成路线中的序号：(IV)1) By a stepwise conversion of spergualin to DSG in the following sequence: a) Protecting the primary and secondary amines of spergualin with N-(benzyloxycarbonyloxy)suc cinimide to form the N,N'-benzyloxycarbonyl derivative (I); b) protecting the 11-hydroxy group with 3,4-dihydro-2H-pyran to the 11-O tetrahydropyranyl derivative (II); c) converting the 1,5-hydroxy function of (II) to a 1,5-mesylate (III); d) halogenation of (III) with sodium iodide, followed by catalytic hydrogenation, to give 15-deoxy-1-O-tetrahydropyranylspergualin (IV); e) hydrolysis of (IV) with p-toluenesulfonic acid in water to yield 1,5-deoxyspergualin. The overall yield of DSG is 1.8%, based on the amount of spergualin used.
| 【1】 Takeuchi, T.; Umezawa, H.; Iwasawa, H.; Ikeda, D.; Kondo, S.; Synthesis of (-)-15-deoxyspergualin and (-)-spergualin-15-phosphate. J Antibiot 1982, 35, 12, 1665-1669. |
| 【2】 Kondo, S.; Takeuchi, T.; Umezawa, H. (Microbial Chemistry Research Foundation); (-)-15-Deoxyspergualin, a process for the preparation of the same, an intermediate of the same, and its use as medicament. EP 0094632 . |
| 【3】 Cheng, C.C.; Zee-Cheng, R.K.-Y.; Deoxyspergualin. Drugs Fut 1987, 12, 2, 113. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 13684 | 3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran | 110-87-2 | C5H8O | 详情 | 详情 | |
| 62979 | benzyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate | C12H9NO4 | 详情 | 详情 | ||
| Spergualin | 62980 | 7-{[amino(imino)methyl]amino}-N-[2-({4-[(3-aminopropyl)amino]butyl}amino)-1-hydroxy-2-oxoethyl]-3-hydroxyheptanamide | C17H37N7O4 | 详情 | 详情 | |
| (I) | 22886 | benzyl 21-amino-4-[(benzyloxy)carbonyl]-11,15-dihydroxy-21-imino-10,13-dioxo-4,9,12,20-tetraazahenicos-1-ylcarbamate | C33H49N7O8 | 详情 | 详情 | |
| (II) | 22887 | benzyl 21-amino-4-[(benzyloxy)carbonyl]-15-hydroxy-21-imino-10,13-dioxo-11-(tetrahydro-2H-pyran-2-yloxy)-4,9,12,20-tetraazahenicos-1-ylcarbamate | C38H57N7O9 | 详情 | 详情 | |
| (III) | 22888 | benzyl 15-(4-[[amino(imino)methyl]amino]butyl)-4-[(benzyloxy)carbonyl]-10,13,17-trioxo-11-(tetrahydro-2H-pyran-2-yloxy)-16,18-dioxa-17lambda(4)-thia-4,9,12-triazanonadec-1-ylcarbamate | C39H59N7O11S | 详情 | 详情 | |
| (IV) | 22889 | 7-[[amino(imino)methyl]amino]-N-[2-([4-[(3-aminopropyl)amino]butyl]amino)-2-oxo-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]heptanamide | C22H45N7O4 | 详情 | 详情 |