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【结 构 式】

【分子编号】22888

【品名】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

【CA登记号】

【 分 子 式 】C39H59N7O11S

【 分 子 量 】834.00404

【元素组成】C 56.17% H 7.13% N 11.76% O 21.1% S 3.84%

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:(III)

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
Extended Information