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【结 构 式】 
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【分子编号】53797 【品名】(5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl benzoate 【CA登记号】n/a |
【 分 子 式 】C34H50O4 【 分 子 量 】522.7686 【元素组成】C 78.12% H 9.64% O 12.24% |
合成路线1
该中间体在本合成路线中的序号：(CXIX)Alcohol (CXII) was converted to aldehyde (CXIII) either by Swern oxidation or by means of NaOCl and TEMPO. The Horner-Emmons condensation of phosphonate (CXV) (prepared from bromo ketone (CXIV) and triethyl phosphite) with aldehyde (CXIII) furnished the unsaturated ketone (CXVI). Asymmetric reduction of the carbonyl group of (CXVI) was accomplished by means of borane-dimethyl sulfide complex in the presence of (S)-MeCBS, yielding (CXVII). Catalytic hydrogenation of the resultant allylic alcohol (CXVII) afforded (CXVIII). The ethylene ketal group of (CXVIII) was then hydrolyzed under acidic conditions to the ketone (CXIX).
| 【1】 Zhang, X.; et al.; Synthesis of squalamine utilizing a readily accessible spermidine equivalent. J Org Chem 1998, 63, 23, 8599. |
| 【2】 Kinney, W.A.; Meckler, H.; Zhang, X.; Lee, N.; Jones, S.; Rao, M.N.; Bulliard, M. (Genaera Corp.); Stereoselective synthesis of 24-hydroxylated cpds. useful for the preparation of aminosterols, vitamin D analogs, and other cpds.. WO 9824800 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (CXII) | 53790 | n/a | C31H44O5 | 详情 | 详情 | |
| (CXIII) | 53791 | n/a | C31H42O5 | 详情 | 详情 | |
| (CXIV) | 53792 | 1-bromo-3-methyl-2-butanone | 19967-55-6 | C5H9BrO | 详情 | 详情 |
| (CXV) | 53793 | diethyl 3-methyl-2-oxobutylphosphonate | n/a | C9H19O4P | 详情 | 详情 |
| (CXVI) | 53794 | n/a | C36H50O5 | 详情 | 详情 | |
| (CXVII) | 53795 | n/a | C36H52O5 | 详情 | 详情 | |
| (CXVIII) | 53796 | n/a | C36H54O5 | 详情 | 详情 | |
| (CXIX) | 53797 | (5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl benzoate | n/a | C34H50O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(CXIX)Treatment of the OH group of (CXIX) with SO3-pyridine provided sulfate (CXX). The benzoate ester of (CXX) was subsequently hydrolyzed under basic conditions to give (CXXI). Reductive amination of (CXXI) with the cyanodiamine (CXXII) afforded (CXXIII). The cyano group of (CXXIII) was finally reduced to the target amine by catalytic hydrogenation.
| 【1】 Zhang, X.; et al.; Synthesis of squalamine utilizing a readily accessible spermidine equivalent. J Org Chem 1998, 63, 23, 8599. |
| 【2】 Kinney, W.A.; Meckler, H.; Zhang, X.; Lee, N.; Jones, S.; Rao, M.N.; Bulliard, M. (Genaera Corp.); Stereoselective synthesis of 24-hydroxylated cpds. useful for the preparation of aminosterols, vitamin D analogs, and other cpds.. WO 9824800 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (CXIX) | 53797 | (5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-4-hydroxy-1,5-dimethylhexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl benzoate | n/a | C34H50O4 | 详情 | 详情 |
| (CXX) | 53798 | (5S,7R,8R,9S,10S,13R,14S,17R)-17-[(1R,4R)-1,5-dimethyl-4-(sulfooxy)hexyl]-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-7-yl benzoate | n/a | C34H50O7S | 详情 | 详情 |
| (CXXI) | 53799 | (1R,4R)-4-[(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl hydrogen sulfate | n/a | C27H46O6S | 详情 | 详情 |
| (CXXII) | 53800 | 4-[(3-aminopropyl)amino]butanenitrile | n/a | C7H15N3 | 详情 | 详情 |
| (CXXIII) | 53801 | (1R,4R)-4-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-({3-[(3-cyanopropyl)amino]propyl}amino)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-isopropylpentyl hydrogen sulfate | n/a | C34H61N3O5S | 详情 | 详情 |