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【结 构 式】 
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【分子编号】47004 【品名】N-[(3aR,5aS,6S,11S,14S,16aS,18R,22S,25S,26aR)-11-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6,18-dihydroxy-22-[(1R)-1-hydroxyethyl]-14-[(4S,5R)-5-(4-hydroxyphenyl)-2-phenyl-1,3,2-dioxaborolan-4-yl]-5,10,13,16,21,24-hexaoxo-2-phenyltetracosahydro-10H-[1,3,2]dioxaborolo[4,5-t]dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-25-yl]-10,12-dimethyltetradecanamide 【CA登记号】 |
【 分 子 式 】C62H86B2N8O17 【 分 子 量 】1237.03056 【元素组成】C 60.2% H 7.01% B 1.75% N 9.06% O 21.99% |
合成路线1
该中间体在本合成路线中的序号：(II)The reaction of cyclopeptide (I) with phenylboronic acid in THF gives the bis boronate (II), which is reduced at the carbamoyl group with BH3/S(Me)2 in THF and deprotected with HCl to afford the cyclopeptide (III). The reaction of (III) with thiophenol and TFA in acetonitrile affords the phenylsulfanyl derivative (IV), which is finally treated with ethylenediamine to afford the target compound. Alternatively, cyclopeptide (I) can be reduced directly to cyclopeptide (II) with BH3/S(Me)2 in THF.
| 【1】 Hugues, D.L.; Belyk, K.M.; Black, R.M.; Bender, D.R.; Leonard, W. (Merck & Co., Inc.); Process for preparing certain aza cyclohexapeptides. US 5552521 . |
| 【2】 Belyk, K.M.; Black, R.M.; Hugues, D.L.; Bender, D.R.; Leonard, W. (Merck & Co., Inc.); A process for preparing certain aza cyclohexapeptides. WO 9624613 . |
| 【3】 Leonard, W.; Belyk, K.M. (Merck & Co., Inc.); A process for preparing certain aza cyclohexapeptides. WO 9747645 . |
| 【4】 Leonard, W.; Belyk, K.M. (Merck & Co., Inc.); Process for preparing certain aza cyclohexapeptides. US 5936062 . |
| 【5】 Kaufman, M.J.; Hunke, W.A.; Neururkar, M.J. (Merck & Co., Inc.); Antifungal compsns.. US 6136783 . |
| 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) | 47003 | N-[(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C50H80N8O17 | 详情 | 详情 | |
| (II) | 47004 | N-[(3aR,5aS,6S,11S,14S,16aS,18R,22S,25S,26aR)-11-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-6,18-dihydroxy-22-[(1R)-1-hydroxyethyl]-14-[(4S,5R)-5-(4-hydroxyphenyl)-2-phenyl-1,3,2-dioxaborolan-4-yl]-5,10,13,16,21,24-hexaoxo-2-phenyltetracosahydro-10H-[1,3,2]dioxaborolo[4,5-t]dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-25-yl]-10,12-dimethyltetradecanamide | C62H86B2N8O17 | 详情 | 详情 | |
| (III) | 47005 | N-[(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C50H82N8O16 | 详情 | 详情 | |
| (IV) | 47006 | N-[(2R,6S,9S,11R,12R,14aS,15S,20S,23S,25aS)-20-[(1R)-3-amino-1-hydroxypropyl]-23-[(1S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,15-trihydroxy-6-[(1R)-1-hydroxyethyl]-5,8,14,19,22,25-hexaoxo-12-(phenylsulfanyl)tetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl]-10,12-dimethyltetradecanamide | C56H86N8O15S | 详情 | 详情 |