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【结 构 式】 
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【分子编号】23671 【品名】2-[(3R,6S,9S,14S,17S,18S)-17-amino-9,14-diisobutyl-3,18-dimethyl-2,5,8,11,13,16-hexaoxo-12-(triphenylphosphoranylidene)-1-oxa-4,7,10,15-tetraazacyclooctadecan-6-yl]acetamide 【CA登记号】 |
【 分 子 式 】C43H55N6O8P 【 分 子 量 】814.919102 【元素组成】C 63.38% H 6.8% N 10.31% O 15.71% P 3.8% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The tert-butoxycarbonyl and 4,4'-dimethoxybenzhydryl groups of (XII) were then deprotected using trifluoroacetic acid, and the resulting compound (XIII) was coupled with the phenylacetyl dipeptide (XIV) to form (XV). Finally, the phosphorus ylide of (XV) was transformed to the desired carbonyl function by means of ozonolytic cleavage of the C=P double bond.
| 【1】 Wasserman, H.H.; et al.; The chemistry of vicinal tricarbonyls: Total syntheses of elastase inhibitors YM-47141 and YM-47142. Helv Chim Acta 2000, 83, 9, 2607. |
| 【2】 Wasserman, H.H.; et al.; Total syntheses of depsipeptide elastase inhibitor. J Am Chem Soc 1999, 121, 6, 1401. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 23670 | C49H65N6O10P | 详情 | 详情 | ||
| (XIII) | 23671 | 2-[(3R,6S,9S,14S,17S,18S)-17-amino-9,14-diisobutyl-3,18-dimethyl-2,5,8,11,13,16-hexaoxo-12-(triphenylphosphoranylidene)-1-oxa-4,7,10,15-tetraazacyclooctadecan-6-yl]acetamide | C43H55N6O8P | 详情 | 详情 | |
| (XIV) | 23672 | (2S,3S)-3-hydroxy-2-([(2S)-3-phenyl-2-[(2-phenylacetyl)amino]propanoyl]amino)butyric acid | C21H24N2O5 | 详情 | 详情 | |
| (XV) | 23673 | (2S,3S)-N-[(3R,6S,9S,14S,17S,18S)-6-(2-amino-2-oxoethyl)-9,14-diisobutyl-3,18-dimethyl-2,5,8,11,13,16-hexaoxo-12-(triphenylphosphoranylidene)-1-oxa-4,7,10,15-tetraazacyclooctadecan-17-yl]-3-hydroxy-2-([(2S)-3-phenyl-2-[(2-phenylacetyl)amino]propanoyl]amino)butanamide | C64H77N8O12P | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIII)The tert-butoxycarbonyl and 4,4'-dimethoxybenzhydryl groups of (XII) were then deprotected using trifluoroacetic acid, and the resulting compound (XIII) was coupled with the isovaleryl dipeptide (XIV) to form (XV). Finally, the phosphorus ylide of (XV) was transformed to the desired carbonyl function by means of ozonolytic cleavage of the C=P double bond.
| 【1】 Wasserman, H.H.; et al.; The chemistry of vicinal tricarbonyls: Total syntheses of elastase inhibitors YM-47141 and YM-47142. Helv Chim Acta 2000, 83, 9, 2607. |
| 【2】 Wasserman, H.H.; et al.; Total syntheses of depsipeptide elastase inhibitor. J Am Chem Soc 1999, 121, 6, 1401. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 23670 | C49H65N6O10P | 详情 | 详情 | ||
| (XIII) | 23671 | 2-[(3R,6S,9S,14S,17S,18S)-17-amino-9,14-diisobutyl-3,18-dimethyl-2,5,8,11,13,16-hexaoxo-12-(triphenylphosphoranylidene)-1-oxa-4,7,10,15-tetraazacyclooctadecan-6-yl]acetamide | C43H55N6O8P | 详情 | 详情 | |
| (XIV) | 23674 | (2S,3S)-3-hydroxy-2-([(2S)-2-[(3-methylbutanoyl)amino]-3-phenylpropanoyl]amino)butyric acid | C18H26N2O5 | 详情 | 详情 | |
| (XV) | 23675 | (2S,3S)-N-[(3R,6S,9S,14S,17S,18S)-6-(2-amino-2-oxoethyl)-9,14-diisobutyl-3,18-dimethyl-2,5,8,11,13,16-hexaoxo-12-(triphenylphosphoranylidene)-1-oxa-4,7,10,15-tetraazacyclooctadecan-17-yl]-3-hydroxy-2-([(2S)-2-[(3-methylbutanoyl)amino]-3-phenylpropan | C61H79N8O12P | 详情 | 详情 |